20 Best Battles In The Pokémon Anime Series

If there's one thing we love more than the pocket monsters themselves, it's seeing them scrapping.

pokemon battle

For over 20 years now Pokémon has been one of the biggest media franchises of all time, with dozens of video games, an anime series which has been running for over 1000 episodes, 22 films (including one live-action), and an ever-expanding trading card game. After 22 years and over 1000 episodes, the anime series has gained all manner of different reactions.

Many people have stuck with it through thick and thin (the Unova saga was a particularly painful time, but it was worth enduring for the subsequent Kalos saga), whereas others stopped watching it after the original series, due to their dislike for Generation II Pokémon. Regardless of whether you feel that the anime peaked quality-wise with the original series, or whether you have continued to watch it to this very day, it is impossible to deny that there have been a number of outstanding Pokémon battles over the years.

And is that not a key factor in our love for Pokémon (anime and games alike)? When playing the games, no matter how attached we grow to the team that we have raised, we love battling with them. When watching the anime, it does not matter how invested we become in Ash and his friends as characters, it is the battles that they partake in which we find most exhilarating. So, to commemorate the upcoming Alola League arc of the anime series, this piece is going to discuss the 20 best battles in the Pokémon anime series to date, reflecting on exhilarating moments and also battle moments which had significance to the characters partaking in said battle.

 

20. Ash vs. Jeanette

What better way to kick off a list of the best battles in the anime than with a real trip down memory lane? Ash grew a fair amount during his Kanto journey back in the original series and, by the time that he faced Jeanette in the fourth round of the Kanto League, he had some well earned victories under his belt. However, his battle against Jeanette was the first in the League Conference in which he did not have Misty and Brock coaching him, and the result was the best battle of that entire League.

The battle started off in Ash’s favour, with his Bulbasaur battling fiercely and taking down Jeanette’s Beedrill and Scyther, reminding fans that he was one of the greatest assets to Ash’s original team. The tides, however, quickly turned when Jeanette’s Bellsprout took out Ash’s Bulbasaur and Pikachu in quick succession, a major upset which nobody saw coming (especially Ash). However, our hero had a trump card – Muk. Not only did Muk’s squishy body absorb Bellsprout’s attacks, but it defeated the Grass/Poison-type by smothering it with a Body Slam, in a victory which countless fans still regard as one of the most amusing wins in the anime over 20 years later.

 

19. May vs. Harley (Hoenn Grand Festival)

What was so refreshing about the Hoenn saga was that Ash was not the only protagonist to have a campaign feature prominently in the group’s regional journey, with May’s Contests and Grand Festival campaign serving as an ongoing storyline. While May developed a friendly rivalry with Drew, her other rival Harley was far more antagonistic towards her and would resort to underhanded tactics. The prime example of this was in the Hoenn Grand Festival’s Appeals Stage, when Harley took advantage of May’s trusting and naive nature by pretending to be her friend and convincing her to continually command Skitty to use Assist, which nearly cost May her Appeal.

May, however, ensured that Harley got his comeuppance when they faced each other in the first round of the Battle Stages. In a double battle, May’s Beautifly and Bulbasaur faced Harley’s Cacturne and Banette. While Harley’s creepy Pokémon initially caused damage to May’s team, Beautifly and Bulbasaur managed to secure the win through their excellent teamwork (emphasising how capable a double-battler May had become) and a dazzling display of their moves, including a beautifully animated Razor Leaf/Silver Wind combination. While May defeated Harley multiple times in Hoenn and Kanto, no other victory against him felt quite as sweet or triumphant due to the sheer pleasure that the viewer felt in seeing Harley get his comeuppance.

 

18. Kiawe vs. Brock/Ash vs. Misty

pokemon battle

Despite taking place during the Alola saga, these battles actually took place in Kanto when Ash and his classmates went there for a field trip in a nostalgic two-parter which, fittingly, aired in 2017 – 20 years after the anime began. After reuniting with Ash, Misty and Brock teach his classmates about Gym battles (something which they do not have in the Alola region) and decide to have a battle each – Kiawe vs. Brock, followed by Ash vs. Misty. Despite Mega Evolving his Steelix, Brock had a disadvantage against Kiawe and his Turtonator, but the subsequent battle was nevertheless an intense one with both trainers giving it their all.

The ending came as a huge surprise – despite being hit by Turtonator’s Z-Move Inferno Overdrive, Mega Steelix shook off the powerful attack and defeated the Fire/Dragon-type with Stone Edge. Not only did this outcome remind fans that, in Pokémon battling, type-advantages do not guarantee a win, but it was a lovely reminder for long-term fans of the anime that, despite battling nowhere near as frequently as Ash, Brock was a strong trainer and a skilled battler.

The following battle between Ash and Misty was just as spectacular, but evoked a far greater sense of nostalgia than Brock and Kiawe’s. Ash and Misty battled each other several times during their journeys together in Kanto and Johto, so to see them face off against each other again for the first time in well over a decade was an absolute joy of a trip down memory lane. The battle between Ash’s Pikachu and Misty’s Mega Gyarados was a great showdown between two powerhouse Pokémon, culminating in Pikachu defeating the Water/Dark-type with his Z-Move, Gigavolt Havoc.

Not only did this battle serve as a lovely trip down memory lane for long-term anime fans, but it was also wonderful to see how accomplished a trainer Misty had become in her masterful control of Gyarados, a species which she had been scared of during her journey with Ash years earlier.

 

17. Ash vs. Winona

Battles against Flying-type Gym Leaders are always among the best Gym battles of their respective regions in the anime, as the fact that at least half of the battlers are airborne offers greater scope to the animators. Not only do the open skies not pose the same physical confinements as a typical battlefield, but the animators can also experiment with a bird’s eye perspective of the world below.

Ash’s battle against Falkner kicked off his campaign against the Johto Gyms very well, while his battle against Skyla was one of his only Unova Gym battles that did not cause viewers to facepalm. The best of Ash’s three Gym battles against Flying-type Leaders to date, however, was the second one against Winona of the Fortree City Gym in Hoenn. For viewers who had played the Generation III games, the fact that Winona proved to be a tough opponent alone was very pleasing as, in the games, Winona is one of the easiest Gym Leaders to defeat for any player who has an Electric-type.

The battle started off with Ash sending out his Grovyle against Winona’s Altaria, with Ash showing his faith in the Grass-type to overcome a type-disadvantage for the second time in his Hoenn Gym campaign. Ash’s faith in Grovyle paid off as he used his speed to dodge Altaria’s attacks, before defeating it with a powerful Leaf Blade. When Pikachu went up against Pelipper, however, Winona proved that she was just as capable of overcoming a type-disadvantage and of adopting an unorthodox strategy, as she had the Water/Flying-type drive its Steel Wing into the ground to render Pikachu’s Electric attacks ineffective. While Pikachu eventually took down Pelipper, he only managed a tie.

The final round was a spectacular aerial battle between Ash’s Swellow and Winona’s shiny Swellow. With a fast pace and excellent animation, it was a tough battle in which Ash’s Swellow eventually came out on top, having endured such powerful attacks as Aerial Ace and Hyper Beam. Not only was this an excellent battle in its own right, but this battle has added significance as battling Winona’s Swellow inspired Ash to teach his Swellow Aerial Ace, which went on to become its signature move.

 

16. Ash vs. Conway

pokemon battle

While he had never really been a rival to them, Ash, Brock and Dawn had become well acquainted with Conway after meeting him several times on their Sinnoh journey. While he was quite an oddball, he was also remarkably intelligent and took a very strategic approach to Pokémon battles. As such, when he faced off against Ash in the third round of the Sinnoh League, Conway proved to be a very tough opponent to beat.

Having spied on Ash preparing for the battle, Conway assumed that Ash would opt for pure power by using Infernape, Torterra and Glalie, so he chose to use Pokémon that were slow and defensive – Shuckle, Lickilicky and Dusknoir. Despite Ash using Noctowl, Donphan and Gible instead (which surprised Conway), he really forced Ash to think outside of the box.

Thinking outside of the box has been a recurring theme of Ash’s Gym and League battles since his first journey through Kanto, but rarely has it led to such absurd moments as those in this battle. Gible stopping Shuckle’s Gyro Ball by catching the Bug/Rock-type in his mouth before he fired it into the air with Draco Meteor is an absurdly brilliant moment, although the most hilarious moment of absurdity is in the battle’s culmination.

It eventually came down to Gible vs. Dusknoir, with the latter having the upper-hand after it used (the beautifully animated) Trick Room to give itself a speed advantage. Ash once again used Gible’s jaw to his advantage by having the Dragon/Ground-type bite down on Dusknoir’s Shadow Punch. This is a hilariously absurd moment, not least because of Conway’s horrified exclamation of “Ah! What kind of move is that? It ate the Shadow Punch!”, moments before Gible won the match for Ash, in what remains the little Pokémon’s finest moment to date.

 

15. Ash vs. Maylene

When Ash and the group arrived in Veilstone City, with Ash planning to earn his third Sinnoh Gym badge, they discovered that Ash’s rival Paul had already been there and defeated Maylene, who had only been the Gym Leader for six months. Not only had he defeated her in a landslide victory, but he had uncaringly belittled her afterwards, causing her to lose confidence in her potential as a Gym Leader. After winning an unofficial match against Dawn, Maylene regained confidence in her potential to be a Gym Leader and agreed to an official battle with Ash.

Ash got off to a very good start as, despite his Chimchar being rendered confused by Maylene’s Meditite, his Staravia was able to take out both Maylene’s Machoke and Meditite, mastering Brave Bird in the process, in the first battle in which the Normal/Flying-type really shined. However, Maylene’s Lucario proved to be the Gym Leader’s MVP, in the first of several occasions in the anime where Ash has struggled to defeat a Lucario. The Fighting/Steel-type defeated Staravia and Chimchar in quick succession, before having an intense battle with Ash’s Buizel, in which the Water-type learnt Water Pulse and activated his Swift Swim ability.

The two Pokémon gave it their all, with Buizel showing just how powerful a battler he was in his first major battle under Ash’s command. While it eventually ended in a tie, the two Pokémon having given it their all, this was a fast-paced, exciting and intense battle, which demonstrated beyond any shadow of a doubt how perfectly suited Ash and Buizel are for each other (after Buizel was traded to Ash by Dawn for his Aipom 13 episodes earlier). Furthermore, the battle cemented Maylene’s restored confidence in her potential and abilities as a Gym Leader even more than her battle with Dawn had. She deemed it the best Gym battle of her life, and many fans have subsequently come to regard it as the best Gym battle of the Sinnoh saga.

 

14. Dawn vs. May

When Dawn became Ash’s new travelling companion at the start of his Sinnoh journey, fans were pleased to see that he would be travelling with another Pokémon Coordinator, as May’s Contest campaigns in Hoenn and Kanto had made for a number of excellent episodes. Despite her mother, Johanna, having won the Sinnoh Grand Festival years ago, Dawn had a lot to learn.

After her first Contest victory, she failed to make it past the Appeals Round in two consecutive Contests, which massively impacted her self-confidence. For the Wallace Cup, a multi-regional Contest tournament, May came over from Johto to partake and joined Ash, Brock and Dawn. She and Dawn both entered and, after multiple tough battles, made it to the final round.

In the final, Dawn sent her Piplup out to battle May’s Glaceon, who was a far more experienced battler. Despite a shaky start, which saw Piplup briefly become paralysed, Dawn managed to hold her own in an exciting battle, with moments such as Piplup deflecting Ice Shard with Whirlpool and destroying Shadow Ball with Peck serving as very good examples of how creative and stunningly animated Contest Battles often were in the anime.

It was a very close match, with Dawn only just scraping a victory in the closing moments, thereby winning the Wallace Cup. Not only was this a spectacular battle between two fan-favourite protagonists, but Dawn’s victory broke her losing streak and helped her regain self-confidence in her future as a Coordinator, concluding a several month storyline which had made her a much more well-rounded character.

 

13. Ash vs. Alain (Kalos League)

pokemon battle

Of all of the Pokémon battles on this list, this is the one which proved to be the most controversial with the anime’s fanbase when it first aired. During the latter part of Ash’s Kalos journey, he had battled his friendly rival Alain several times but never won, his Greninja (even in its Ash-Greninja form) losing to Alain’s Mega Charizard X every time. In the time since their last battle, however, Greninja had mastered its Ash-Greninja form and become quite possibly Ash’s most overpowered Pokémon of all time.

Furthermore, rivals who had defeated Ash on multiple occasions (e.g. Paul and Trip) had always lost to him in their League Conference battle, while the Japanese episode title for the final part of their Kalos League battle translated to “Kalos League Victory! Ash’s Ultimate Match!” As such, fans were under no uncertainty that Ash would defeat Alain in the Kalos League final and finally win a League Conference (other than the Orange League).

When an intense and fairly even battle between Ash and Alain culminated in Mega Charizard X once again defeating Ash-Greninja after an explosive clash of Blast Burn and Water Shuriken, fans were outraged to see Ash only become the runner-up, and the episode currently holds a mere 4.3/10 on IMDb. Despite an outcome which left countless fans disappointed, this is nevertheless an excellent battle. It is a fairly even match between the two, with a number of great moments, such as Ash’s Talonflame and Alain’s Unfezant having a spectacularly animated aerial battle, and Pikachu once again proving himself to be Ash’s MVP by taking out Alain’s Tyranitar and Metagross.

Furthermore, the battle also emphasised the brotherly bond between Ash’s Noivern and Hawlucha, while the conveyance of Ash and Alain’s internal thoughts showed just how much the two rivals had come to respect and admire each other. It may have ended in Ash’s defeat, but the fact that Ash was nevertheless satisfied with an excellent (and close) battle emphasised just how much he had matured during his Kalos journey.

 

12. Ash vs. Noland

When the Kanto Battle Frontier saga first began it was clear that it was ultimately a filler-arc which was veiled with the nostalgia factor which came with it being a return to Kanto – the region where the anime began. However, the first battle of the saga saw Ash take on Frontier Brain Noland, in a battle which made it clear that, despite ultimately being a filler-arc, the Kanto Battle Frontier saga would boast some excellent Pokémon battles.

When Ash and the group first meet Noland, the Frontier Brain tells Ash that he can choose one of Noland’s Pokémon to battle in a one-on-one match. Ash chose to battle the Legendary Articuno, a Pokémon which Noland was close friends with but did not officially own, and to battle the Ice/Flying-type Ash brought his powerhouse Charizard back to his team.

Despite not officially being Noland’s Pokémon, Articuno showed the Frontier Brain unquestioning loyalty and trust, obeying his every command and proving that it was not a Legendary Pokémon for nothing. Despite a type-advantage, Charizard did struggle against Articuno as he was hit by a powerful Water Pulse and had his aerial abilities slowed down after Articuno froze part of his wing. Furthermore, Articuno even managed to counter Charizard’s powerful Overheat.

After an intense match, it looked like Charizard would lose until Ash had him grab Articuno by the wings and slam it into the ground with his signature finisher – Seismic Toss. An exhausted Charizard was only just about able to stand, but he had done enough to defeat Articuno, securing Ash his first Frontier Symbol and his first ever victory against a Legendary Pokémon. An intense match, not only was it a joy to see Charizard and Ash battle together again for the first time in 3 years, but it built anticipation for Ash’s future Battle Frontier matches.

 

11. Ash vs. Clemont (Gym Battle)

pokemon battle

When Ash first arrived in the Kalos region, he was barred from challenging the Lumiose Gym as he did not have four Kalos region Gym badges yet. A few episodes later, he learned that his new travelling companion, Clemont, was the Lumiose Gym Leader and had programmed a robot, Clembot, to take over as Gym Leader. After repairing Clembot so that it no longer barred trainers with less than four badges from challenging the Gym, Clemont agreed to be the Lumiose Gym Leader whom Ash would challenge, after he had won four badges. As such, by the time that Ash and Clemont finally had their Gym battle, fans of the series had been anticipating it for over a year, a sense of anticipation heightened by the fact that Clemont had briefly left the group a few episodes earlier to return to Lumiose City and prepare for the battle.

While this was the fifth time that Ash had battled an Electric-type Gym, this is the one for which the term electrifying feels most apt. Fast-paced and energetic, with trainers and Pokémon alike bringing passion and determination to the match, it is an exciting battle to watch, while the animation is another example of how the Kalos saga benefitted from not having stock effect backgrounds during battles. Clemont proved himself to be a very formidable opponent, with even his Normal-type Bunnelby having the powerful Electric-type move Wild Charge in his moveset. After a fierce battle in which Pikachu and Hawlucha defeated Clemont’s Bunnelby and Heliolisk respectively, it eventually came down to Goodra vs. Luxray, the latter having already defeated Hawlucha and Pikachu.

In an intense battle which saw Luxray briefly boost his Attack power with Electric Terrain (before Goodra nullified the Terrain with Rain Dance), Goodra eventually came out on top, finishing the Electric-type off with an explosive Bide. Altogether this was a terrific Gym battle, which most certainly lived up to the hype which had built up about it on Pokémon fan forums for over a year. Furthermore, it established to viewers beyond any shadow of a doubt just how capable a battler Clemont is, while it was also a treat to see Goodra (Ash’s first and, so far, only Pseudo-Legendary) show how far it had come from the weak and timid Goomy which Ash had caught only a few months earlier.

 

10. Ash vs. Clair

While their initial attempt at a Gym battle had been rudely interrupted by Team Rocket (classic Team Rocket), Ash nevertheless saw that Blackthorn Gym Leader Clair’s Dragon-type Pokémon were a force to be reckoned with, so for their second battle he chose his team with real power battling in mind. As well as Pikachu, Ash brought his powerhouses Charizard and Snorlax back to his team to take on Clair’s Kingdra, Gyarados and Dragonair, a decision which ultimately foreshadowed the fact that Charizard and Snorlax would go on to be the MVPs of Ash’s Johto League battles.

Snorlax and Pikachu managed to defeat Kingdra and Gyarados respectively in exciting battles, with the former emphasising the fact that Snorlax has a very useful combination of great defensive capabilities and brute strength, and the latter providing another good example of how Pikachu has often used his speed to his advantage in battle. However, the battle’s climax is when it became the most memorable as Charizard faced off against Dragonair, in another excellent example of how Ash will often think outside of the box in battle.

To prevent Dragonair from hiding in the pool, Charizard used Flamethrower and Fire Spin to evaporate the water, before defeating the Dragon-type with a spectacular Fire Spin/Seismic Toss combination. Not only was this a terrific wrap-up to an excellent Gym Battle, but it ultimately served as a foreshadowing of an unorthodox technique which Ash and Charizard would use in the Johto League.

 

9. Ash vs. Brandon (Final Battle)

While the Battle Frontier saga was ultimately a filler-arc that filled the wait until the release of the Generation IV games, it was impossible not to invest in Ash and May’s respective Battle Frontier and Grand Festival campaigns in Kanto, as we were given some excellent battles. Having already won six Frontier Symbols, Ash found that the final Frontier Brain, Brandon, was the toughest yet and lost to him in two consecutive battles. For his third (and final) effort to defeat Brandon, our hero brought back Bulbasaur, Charizard and Squirtle to his team and, along with Pikachu, decided that he would use what remained of his original team to defeat this tough opponent.

This was a battle that ultimately served as a tribute to anime fans who had been with the series since Ash first began his journey, as seeing Pikachu, Bulbasaur, Charizard and Squirtle all battling together for the first time in almost 7 years evoked a real sense of nostalgia for the original series. Seeing Brandon’s Dusclops defeat Charizard early on in the battle was very unexpected and did not bode well for Ash, but what followed was an exciting and tense match in which Bulbasaur and Squirtle between them managed to take down Dusclops, Ninjask and Solrock.

Eventually it came down to Brandon’s Legendary Regice battling Ash’s Pikachu in a very close match, but the Electric-type eventually came out on top, securing his first ever defeat of a Legendary. To watch Ash’s oldest team members battle so fiercely and come out on top was an absolute joy to watch, and the battle ultimately served as three things – a fitting conclusion to Ash’s Battle Frontier campaign, a nostalgia-evoking tribute to long-term fans of the anime, and an all time great Pokémon battle in its own right.

 

8. Ash vs. Blaine (Rematch)

Ash generally struggled in his Kanto Gym battles due to his inexperience, and his initial battle with Cinnabar Gym Leader Blaine was no exception. Blaine defeated Ash with ease, mainly because Ash’s disobedient Charizard could not be bothered battling. However, Ash and Charizard would later help Blaine and his Magmar in preventing the volcano within which the Gym was located from erupting. As they worked together, Charizard observed just how strong Magmar was and saw a Pokémon whom he believed would make a worthy opponent, a feeling which Magmar reciprocated. Seeing this, Blaine agreed to give Ash a rematch atop the volcano, with Charizard even being willing to listen to Ash for the battle.

What we were given was a fast-paced, intense and fiery match between two powerful Pokémon. The fact that Magmar lived in the volcano gave it the upper hand for a fair amount of the battle, as it was able to maneuver around its home very well and even managed to drag Charizard into the lava. Charizard, however, proved himself to be a very tough opponent, unwilling to go down without a fight – a particularly memorable moment being when he actually catches Magmar’s powerful Fire Blast just as it is about to hit him.

Ultimately Charizard won the battle, using his aerial abilities to his advantage and defeating Magmar with a powerful Seismic Toss. Altogether this remains one of the most intense, exciting and memorable Pokémon battles in the history of the anime over 20 years later, and continues to evoke a sense of nostalgia for long-term fans. Furthermore, this was the first time that Ash’s Charizard used Seismic Toss, which would go on to be his signature finisher, and the battle gave fans real hope that Charizard would eventually come to fully obey Ash, a hope which would be fulfilled 46 episodes later.

 

7. Ash vs. Olympia

pokemon battle

Psychic-type trainers having psychic abilities was a concept which had first been explored with Sabrina during the Kanto saga, in one of the darkest moments of the original series, as well as with Anabel in the Kanto Battle Frontier saga. Olympia, however, had more traditional psychic powers as she could see into both the past and the future, which made her quite a compelling character, whose full range of abilities still had an air of mystery by the time that she faced Ash in a Gym battle. Similarly to his Gym battle against Psychic-type trainers Tate and Liza in Hoenn, Ash faced Olympia in a double battle, pitting his Frogadier and Talonflame against her two Meowstic (one Male, one Female).

Within the most breathtakingly designed and animated Gym interior to date, the two teams engaged in a magnificent battle, which exemplified better than any other battle of the Kalos saga how much the series had benefited from the animators no longer using stock effect backgrounds during battles. The two Meowstic were in perfect sync with each other, as the Male boosted the power of the Female’s attacks with Helping Hand, while the Female’s Keen Eye ability boosted the accuracy of her attacks, making it very difficult for Ash’s team. However, Ash’s Pokémon showed great teamwork, with Frogadier taking a Thunder Wave for Talonflame, so that the Fire/Flying-type would not lose its aerial maneuverability, which it in turn used to prevent the Water-type from sustaining serious injuries and navigate above the battlefield.

In the climax of the spectacular and suspenseful battle between the two teams, Ash did something which neither Olympia nor the viewers could have foreseen – he had Pikachu sense when the Future Sight was coming so that his Pokémon could throw the Meowstic into the path of their own attack. While long-term fans of the anime have become accustomed to Ash’s unorthodox methods, none of us had imagined one quite like this. After that it did not take Ash’s Pokémon long to defeat Olympia’s, making this not only one of the best Gym Battles in the anime series to date, but also the finest double battle and one of, if not the, most beautifully animated as well.

 

6. Ash vs. Lt. Surge (Rematch)

When looking back on the first half of the Kanto saga now, over 20 years after it first aired, it’s crazy to think how few of Ash’s early Gym badges he actually earned by winning fair and square. In fact, of his first five Gym badges, he only won one by defeating the Gym Leader in battle, a feat which he achieved in his rematch against Lt. Surge at the Vermilion City Gym. Ash’s first battle against Surge barely lasted a minute as Pikachu was easily outmatched by his evolved form – Raichu.

Following the battle, Ash considered evolving Pikachu so that he would stand a chance against Raichu, but did not want to as he did not want to adopt Surge’s viewpoint that Pokémon should be made to evolve for the sake of brute power. Fortunately, Pikachu agreed with Ash as he wanted to defeat Raichu by his own merit, so the two came up with a strategy that would be unveiled in their rematch.

When Ash went for his rematch against Surge, the Gym Leader was very sceptical and laughed at Ash for thinking that he could win with an unevolved Pokémon. However, in their new strategy Ash showed just how much he had come to understand Pikachu and his skills, in the first of many occasions in the anime which prove that brute strength alone is not enough to win a Pokémon battle, which really speaks to fans who play the games and have learnt the importance of strategic battling.

Using Quick Attack and Agility to dodge Raichu’s attacks, Pikachu soon exhausted the much slower Pokémon and even absorbed Raichu’s electricity into his tail, which he then slammed into his evolved form, knocking it out. This serves as a significant battle, not just because it showed a real turning point for Ash as he won a Gym battle fair and square for the first time, but also because it is the first real example of Ash and Pikachu adopting an unorthodox strategy to win a battle, establishing a motif which has defined Ash’s approach to battling ever since.

 

5. Ash vs. Sawyer (Kalos League)

pokemon battle

Of all of the rivals Ash has had over the course of his journey, very few of his rivalries have been as friendly as that which he had with Sawyer, a beginning trainer from Hoenn who had travelled to Kalos to earn Gym badges and take on the Kalos League. After they first met, it became clear that Sawyer admired and respected Ash, and the two battled whenever they met.

Despite losing every time, Sawyer visibly grew as a trainer as he learned from previous battles, while his Sceptile developed a rivalry with Ash’s Greninja. He eventually defeated Ash in a battle a few weeks before the Kalos League, but promised that they would battle again at the League, which they did when they both reached the semi-final round and engaged in their first full six-on-six battle against each other.

The English dub title for the first episode in which this battle aired sums up the two trainers perfectly – “Analysis Versus Passion!” Ash has always battled passionately, choosing to go with his gut and adopt unorthodox strategies by thinking outside of the box. Sawyer, however, was always very analytical, observing how his opponents battled and taking notes in order to learn for future battles, and this approach to battling came through as he gave Ash a tough fight. Sawyer used his previous observations of Hawlucha, Talonflame and Pikachu’s battling styles to inform his own strategy when he sent out his Slaking, Clawitzer and Aegislash against them in some spectacularly animated and quite intense battles.

Ash’s Noivern and Goodra then battled Salamence and Slurpuff respectively to explosive ties, as the two trainers gave it their all and showed how far they had come on their Kalos journeys. Furthermore, their internal thoughts are revealed during the battle and reflect to the viewer just how much the two trainers had come to admire and respect each other over the course of their rivalry.

The battle culminated in Ash-Greninja battling Mega Sceptile, with Greninja overcoming a type-disadvantage and narrowly winning the battle for Ash. It was a spectacular battle and a wonderful wrap-up to Ash and Sawyer’s rivalry, which took a mature approach to Pokémon battling as, by the end of the battle, it is clear that the two trainers would have ultimately been okay with losing, as they took joy in battling somebody that they respected in a match where they each gave it their all.

 

4. Ash vs. Drake

The Orange Islands saga was a filler-arc plain and simple, even though we may not have realised it when we first watched the English dub of it back in early 2000 (as an 8-year-old back then, I certainly did not know what a filler-arc was for a series – ah, blissful ignorance). However, we invested into it as, despite some quite unorthodox and unique Gym “battles”, there was an Orange League and we wanted to see Ash have another shot at winning a League Conference, after he lost in the fifth round of the Kanto League.

Rather than the tournament which we had expected, to win the Orange “League” Ash had to defeat the Head of the Orange Crew – Drake. However, it became clear that this would be no easy feat as Drake had never been defeated in battle and his trump card was the Pseudo-Legendary Dragonite, and these facts really built our anticipation for their battle.

The battle would be Ash’s first ever full six-on-six battle (a stage which he disappointingly never reached in the Kanto League), and Ash’s team gave it their all. The battle got off to an excellent start as Ash showed just how much he had grown as a trainer during his journey so far. Pikachu faced off in a tough match against Drake’s Ditto, while Lapras fought Drake’s Gengar to an explosive tie, and Tauros came up trumps in his first ever battle by taking down Drake’s Venusaur.

However, Drake was not undefeated for nothing, as his powerhouse Dragonite took out Charizard, Squirtle and Tauros in quick succession (although they all dealt it damage). Pikachu ultimately won after a fierce battle, and Ash became the first ever trainer to defeat Drake. Not only was this a magnificent battle in its own right, but seeing Ash win his first ever full battle emphasised just how much he and his Pokémon had grown in strength, skill and teamwork. It was also an absolute joy to see Ash gain his first ever winner’s trophy for a regional League – here’s hoping that, at the upcoming Alola League, Ash once again manages this feat — 20 years later.

 

3. Ash vs. Harrison

When the Johto League Conference began, Ash and his friends met Harrison, a trainer from the Hoenn Region who had a powerful Blaziken on his team – a Pokémon which Ash had never seen before and which was the latest of several Generation III Pokémon that the group encountered during the Johto Saga in the run-up to the launch of the Generation III games. He and Ash developed a friendly rivalry over the course of the conference, with both trainers there to win the Johto League and coming to see the other as a trainer of merit, who would prove a formidable foe should they come to battle each other. The two eventually got to battle each other in the quarter-finals of the tournament in a full six-on-six battle, by which point Ash’s Johto League campaign had really heated up, following his battle against Gary.

The battle got off to quite an intense start, as Harrison sent out Kecleon (a Generation III Pokémon who Ash had never battled) to battle Pikachu. Not only did Kecleon catch Ash off-guard as it was faster than the Electric-type and able to camouflage with its surroundings, but it was able to cut the grass which Pikachu hid in with its long tongue. After Pikachu eventually defeated Kecleon (after grabbing its tongue), the match became quite fast-paced and a very close match between the two trainers, as well as an excellent example of just how unorthodox Ash’s battling can be.

His Totodile defeated Harrison’s Sneasel by biting down on its Metal Claw and then slamming it into the ground as he danced around, before he defeated the frazzled Dark/Ice-type by slamming his tail into it. Likewise, Ash’s Bayleef overcame a type-disadvantage and defeated Harrison’s Houndoom by muzzling it with her Vine Whip and finishing it off with a Body Slam. The battle also boasted a comic factor, as Ash’s Snorlax was enraged when Harrison’s Hypno used Dream Eater on him, causing him to wake up and take out the Psychic-type with Hyper Beam, in a moment that is amusingly relatable to anybody who values their sleep. Snorlax was also Ash’s MVP in this battle as it took out Harrison’s Steelix too.

Eventually the battle came down to Harrison’s Blaziken against Ash’s Charizard in the only clash to date that was more fiery than Charizard’s battle against Blaine’s Magmar. Not only was it a fiery battle as their elemental-type moves clashed with (at times) explosive results, but Charizard did not even have an aerial advantage, due to Blaziken’s remarkable jumping skills and ability to maneuver mid-air. After Charizard’s most heated battle to date, Blaziken was only just able to stand while Charizard was ultimately defeated, taking Ash out of the tournament.

While Ash may have been defeated, this remains one of his most intense and spectacular battles to date, thanks to the excellent examples of his unorthodox strategies, the comic factor and the fiery final showdown between Charizard and Blaziken. Furthermore, Harrison ultimately inspired Ash to go to the Hoenn region, following the Johto League and, for viewers, to see such a powerful Pokémon as Blaziken (who defeated Charizard just with Fire-type moves – no easy feat) really built anticipation for the types of Pokémon and challenges which Ash would encounter in his next regional journey.

 

2. Ash vs. Paul (Sinnoh League)

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While Ash’s rivalry with Gary will forever remain the most significant to the character, no rival has ever driven Ash in quite the way that his Sinnoh rival, Paul, did. While there were indications that Paul was slowly gaining respect for Ash during the final quarter of the Sinnoh saga, this came after 160 episodes of treating Ash with coldness, belittling somebody whom he viewed as a weak trainer. Paul took a much harsher approach to training Pokémon than Ash did and had defeated him in multiple battles, including a six-on-six match where he defeated all of Ash’s Pokémon while only two of his were knocked out. Ash’s determination to defeat Paul was born from his desire to not only prove himself a trainer of merit, but to prove to Paul that his method of training Pokémon with love and friendship was at least as valid as Paul’s more dictatorial approach to training.

As such, fans of the anime were very excited when the two faced each other in a full six-on-six battle in the Sinnoh League quarter-finals, by which point they had been rivals for 4 years and over 180 episodes. Using the same team who had lost to Paul in their last full battle (Pikachu, Staraptor, Torterra, Infernape, Buizel and Gliscor), for Ash and his Pokémon this battle was not just about proving to Paul that they were worthy opponents, but about proving to themselves that they had grown in strength and skill.

Of Paul’s team (Aggron, Gastrodon, Drapion, Ninjask, Froslass and Electivire), only Electivire had partaken in their last battle, which meant that Paul had the upper-hand as he understood Ash’s team as battlers far better than Ash understood his. Furthermore, it was shown over the course of the battle that Paul had devised his entire strategy after scrutinising how Ash and his team battled, revealing that he took Ash seriously as an opponent, despite considering him predictable.

As a result, the battle itself is an intense one and quite slow-burn in comparison to others (to date it is the only six-on-six battle to ever be spread out across three full episodes). While Ash got off to a very good start by defeating Aggron and Gastrodon with Infernape and Buizel respectively, things got a lot more intense when Drapion took out Buizel, Staraptor and Torterra in quick succession, and also laid down the Toxic Spikes that would later poison Gliscor and Infernape. This left fans on the edge of their seats as it somewhat mirrored how Paul’s Ursaring had swept half of Ash’s team in their last full battle, and we were left wondering how Ash could pull off a victory. However, the latter part of the battle showed Ash thinking outside the box in order to whittle Paul’s team down to Electivire.

Despite it now being three-on-one in Ash’s favour, Electivire proved why it was one of Paul’s powerhouses as it quickly defeated Gliscor, before defeating Pikachu in a moment that served as a throwback to Ash and Paul’s first ever battle when Electivire was still an Elekid. The final showdown between Infernape and Electivire was the most intense of all as the two Pokémon were rivals as, back in their Chimchar and Elekid days when the former was still Paul’s Pokémon, Electivire had bullied Infernape. As the two battled it out in one of the most heated battles imaginable, however, it became clear that the two powerhouse Pokémon had really come to respect each other, with Infernape having proven itself a worthy opponent to Electivire.

Infernape eventually won after activating its Blaze ability, a victory that was satisfying for a number of reasons. Not only was it an outstanding battle with an explosive finish, but it was a fitting wrap-up to an ongoing storyline of 4 years, which saw Paul come to respect Ash as a trainer of merit. Furthermore, it emphasised more than anything else just how far Infernape had come under Ash’s care from the timid Chimchar whom Paul abandoned after deeming weak, serving as a wonderful round-off to Infernape’s character arc.

 

1. Ash vs. Gary (Johto League)

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If you mention the name “Gary Oak” to a long-term fan of the Pokémon anime, then you will evoke a sense of nostalgia as they think back to Ash’s first ever rival – a rivalry which began in the very first episode of the anime. During the Kanto saga, Gary was a very arrogant and obnoxious trainer (just like Blue, his counterpart in the Generation I games). Grandson of Professor Oak, Gary began his Pokémon journey with a greater understanding of Pokémon than Ash and was always a step or ten ahead of our hero, defeating more Gyms than him and catching a wider variety of strong Pokémon than him (many of whom were fully-evolved, unlike most of Ash’s team). Gary also mocked and belittled Ash at every opportunity, which did fuel Ash to push himself further, but also enraged him on several occasions.

While Ash made it further in the Kanto League than Gary did, after the latter was defeated by Melissa (if you cannot remember her then that is fine, she never appeared again afterwards), he had never defeated Gary in a battle. When the two had a one-on-one battle after Ash returned from the Orange Islands, Gary’s Eevee defeated Ash’s Pikachu with ease. However, Gary was a lot more friendly towards Ash, having been humbled by his loss at the Kanto League, although their rivalry remained as the two trainers headed to the Johto region, with both of them determined to win the Johto League. When they arrived at the Johto League, Gary was friendly to Ash but expressed his determination to defeat him, showing that he was still very confident in his abilities.

The two eventually battled each other in a full six-on-six battle for a place in the League’s quarter-finals. Knowing that Gary had a very powerful and well balanced team, Ash put together a team with pure power in mind – in other words brute strength, as this remains the only full battle in which Ash did not use Pikachu. Despite Ash’s Heracross enduring a powerful Fire Blast from Gary’s Magmar before defeating the Fire-type, it became clear early on that Gary had the upper-hand. His powerful Blastoise had no trouble taking out Ash’s Heracross and Bayleef. And despite Ash’s Snorlax showing himself to be a real powerhouse by defeating Nidoqueen and Arcanine without much difficulty, he was defeated by Gary’s powerful Scizor. Eventually, Ash’s Charizard was his only Pokémon left, while Gary still had Scizor, Golem and Blastoise. Charizard, however, proved that he was not Ash’s most powerful Pokémon for nothing, taking out Scizor and Golem in quick succession.

The final showdown between Charizard and Blastoise was the most intense though, as the two powerhouses battled it out in a close match in which Ash really thought outside the box. When Blastoise kept Charizard at bay with Hydro Pump, Ash had the Fire/Flying-type melt the battlefield with Flamethrower, which forced Blastoise to cool the ground down with Hydro Pump, and the resultant steam cloud meant that Charizard could draw close to his opponent. As Blastoise could not aim a Water-type move at Charizard at close-range, it became a physical fight which, for many viewers, evoked a sense of nostalgia for the Generation I games (a.k.a Red vs. Blue).

Eventually Charizard won with his signature Seismic Toss, after what remains the most intense and gripping Pokémon battle in the anime series to date, as well as the most significant battle of the anime series to date. This was Ash’s first ever victory against Gary, after 5 years and 270 episodes, and can ultimately be viewed as the culmination of his entire journey up until that point, as it showed just how far Ash had truly come from the naive trainer who constantly lived in Gary’s shadow. Following the battle, Gary and Ash’s rivalry ended and they became friends, thereby concluding an ongoing storyline in fitting fashion, while the victory gave Ash a new lease of confidence in his skills and potential as a Pokémon Trainer.

Looking forward to more Pokémon content? Read up on this year’s upcoming games and movies, or check out our opinion piece on what we’d like to see in the upcoming Pokémon Sword and Shield.

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