Over the course of eight generations within the Pokémon franchise, Ash has enjoyed and endured all manner of difficult battles over the years, against worthy adversaries and dangerous opponents alike. Ash has so often relied on first losing a battle only to then figure out what he needs to work on. Sometimes, however, he manages to get through difficult bouts even when he seems to be on the verge of defeat.
There are plenty of examples of close battles where Ash has managed to hang in there and squeeze out a victory against the odds, whether it is down to his own strategies or sheer perseverance and determination.
10 Katie Inadvertently Became One Of Ash’s Toughest Opponents Despite Very Little Character Buildup
The Ever Grande Conference is perhaps one of the toughest Pokémon League competitions that Ash has ever taken part in, with them introducing 6-on-6 bouts early on. Ash’s Hoenn campaign is often remembered for his battle against his friend Morrison and his quarter-final loss to Tyson, but his battle against Katie in the top 32 almost sees him make an early exit.
Katie confuses and frustrates Ash with clever strategies and tactical approaches, from keeping an eye on type advantages, to having her Misdreavus take out Ash’s powerful Glalie with Destiny Bond. This is all before introducing her ace, Walrein, which wreaks havoc with its strategy of hitting and then quickly diving into the water to avoid damage. Ash’s Grovyle looks beaten but manages to trick Walrein into freezing the water, giving it the chance to rally and pick up an impressive victory over a tough opponent.
9 Ash Only Just Managed To Overcome Roark’s Mighty Rampardos In Their Rematch
Having already lost to the Oreburgh Gym Leader, Roark, Ash goes into the rematch knowing that, despite his training since their first bout, he now has to face a newly evolved Rampardos, a daunting prospect considering that Cranidos was enough of a problem before.
Sure enough, Rampardos breezes through Ash’s Aipom and Pikachu after Roark has already lost his Onix and Geodude, leaving Rampardos to face off against Turtwig. Rampardos has incredible power and physical offense, with Turtwig taking the full force of this. Yet, against the odds, Turtwig manages to pick up the victory against its much larger opponent.
8 Conway’s Strategy & Cunning Almost Defeated Ash
Ash’s campaign at the Lily of the Valley Conference in Sinnoh is mostly remembered for the exceptional battle with his bitter rival Paul, and the humiliating loss to the powerful Tobias in the following round, but an earlier match between Ash and Conway also deserves a mention.
Conway uses meticulous planning and strategy to make sure that the 3-on-3 becomes a 1-on-1 between the intimidating Dusknoir and Ash’s Gible. Dusknoir has the momentum from defeating Noctowl and Donphan, with it also appearing to have Gible beaten, before Gible’s love for biting things helps it to thwart the Ghost-type and pick up the win for Ash.
7 Ash Needed Charizard To Actually Obey Him In Order To Defeat Blaine
Over the course of his Kanto adventures, Ash is given several of his Gym Badges without really earning them through outright victories, a fact that still annoys many fans to this day. Ash’s seventh Gym battle against Cinnabar Island’s Blaine, however, has an intriguing 3-on-3 contest, even if Charizard’s unreliable nature threatens to ruin that through initially ignoring Ash’s orders.
Charizard eventually opts to fight Magmar when it deems it to be a worthy opponent, and despite the questionable motives, their battle goes right down to the wire. It appears that Magmar has dragged Charizard into the lava to its demise, before Charizard flies up and crashes Magmar back down for the win.
6 Ash & Gary’s Johto Showdown Appeared To Have Ash At A Serious Disadvantage
Gary Oak will always be known as Ash Ketchum’s first rival in the anime, but when considering the extent of the battles and interactions, he can barely be compared to some of Ash’s rivalries across the other generations. Although they haven’t battled too often, their 6-on-6 bout at the Silver Conference in Johto was just the spark that their rivalry needed.
It ultimately boils down to Blastoise versus Charizard, but despite the sever type disadvantage that Ash faces and the excessive amounts of water that Blastoise can aim at his Fire type, he improvises. By having Charizard burn the battlefield, he is able to rescue victory from the jaws of defeat.
5 Roxie Was Disadvantaged By Having Only Three Pokémon But Still Almost Won
The Virbank Gym battle between Roxie and Ash is one of the most intense and closely fought contests of Ash’s entire Unova campaign. The Poison-type Gym Leader insists that Ash uses six Pokémon up against her three, but it still comes down to the wire. Through explosive bursts from her Koffing, Scolipede, and Garbodor, Roxie is able to whittle the fight down to Garbodor versus Pikachu.
Garbodor’s size and power have Pikachu almost beaten, before Pikachu manages to utilize its ability of Static to paralyze Garbodor and turn the tide. This isn’t the end for the formidable Garbodor however, with it rallying once more before Pikachu finally manages to overcome the odds and earn the victory with a barrage of attacks, finishing with an Electro Ball.
4 Ash’s Buizel Managed To Rally Against Maylene’s Lucario & Earn A Draw
Ash Ketchum will always be remembered for receiving his Kanto Gym Badges without actually earning most of them, but, since then, he has fought hard to achieve honorable victories. However, while in Sinnoh, he received the Cobble Badge from Veilstone Gym Leader Maylene, despite their battle resulting in a tie.
When both trainers are down to their last Pokémon, with Maylene having lost Machoke and Meditite and Ash having lost Staravia and Chimchar, Lucario and Buizel face off in an intense showdown. Lucario hits Buizel with plenty of devastating offensive moves and it looks to be down and out, before it learns Water Pulse and reveals its Swift Swim ability, eventually earning a hard-fought tie.
3 Paul Was Close To Another Victory Over Ash, But Infernape’s Blaze Was His Undoing
The final battle between rivals Ash and Paul in the quarter-finals of the Lily of the Valley Conference is still regarded as one of the best battles of the entire Pokémon anime, with the 6-on-6 bout coming right down to the wire, with Infernape against Electivire being the final face-off.
Compared to some of the undeserving trainers who have defeated Ash in Pokémon League matches over the years, Paul is an example of someone who arguably deserved the victory. He approaches it with careful planning, substituting out some of his most trusted partners in the name of exploiting type advantages and disadvantages. Electivire seemingly has Infernape beaten, but Infernape triggers its Blaze ability, defeating Paul with the very ability that he had dedicated his training to perfecting back when Chimchar belonged to him, making it a poetic end to their rivalry.
2 The Third Bout Between Ash & Brandon Was Their Best & Closest Contest
Following his strong showing at the Ever Grande Conference in Hoenn, Ash decides to take that momentum and attempt the Battle Frontier challenge. Brandon is seen as the big boss to defeat at the end, with trainers needing the other six symbols to be able to face him. Brandon easily defeats Ash the first two times, but its the third and final bout that is the most memorable of all.
Ash and Brandon fight 4-on-4, with Ash’s Charizard, Bulbasaur, and Squirtle falling alongside Brandon’s Dusclops, Solrock, and Ninjask, leaving Pikachu versus Regice to decide the battle. The Legendary Titan Regice has Pikachu frozen solid, but just as the referee is preparing to announce Brandon as the winner, Pikachu rallies and picks up the victory against the odds.
1 Gladion Thought He Had Ash’s Lycanroc Beaten Before It Countered A Counter
The Sun & Moon seasons of the anime are revolutionary within the Pokémon franchise, in the sense that they introduce a new region, with a fresh new format away from the Gym Badges of old, leading up to a Pokémon League tournament that Ash eventually wins.
The final of the Manalo Conference sees Ash face off against his rival Gladion, with the 3-on-3 contest boiling down to Lycanroc versus Lycanroc. After a fierce battle, Gladion has his Lycanroc use Counter which is sure to secure his victory, before Ash’s Lycanroc uses Counter in return, picking up the victory in a shocking twist.
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