Ash Ketchum seems to have varying degrees of success with Gym Leaders in every new region that he visits during his grand Pokémon adventure. He breezed his way through Kanto’s finest with him rarely earning his Gym Badges through conventional means and actual Pokémon battles, before showing more improvement in both Johto and Hoenn.
His journey to Sinnoh sees him raise one of his best-ever teams and achieve one of his finest results at the region’s Pokémon League, but the road to the Lily of the Valley Conference wasn’t always easy, with Ash facing multiple tough trainers and Gym Leaders on the way.
8 Crasher Wake Was Outdone By A Stellar Display From Ash
The Pastoria Gym Leader, Crasher Wake’s team looks formidable on paper, but in reality, he loses his Gyarados, Quagsire, and Floatzel without knocking out any of Ash’s Pokémon despite his Buizel and Pikachu being at odds for most of the battle. Ash is able to understand when he is fighting a losing battle and manages to utilize clever substitutions, switching between Turtwig, Buizel, and Pikachu, even having Pikachu and Buizel settle their differences by the end of the bout.
If Ash wasn’t allowed to switch Pokémon, Crasher Wake may well have beaten Turtwig with Quagsire and picked up another win with Floatzel, but the rules permit switches for the challenger.
7 Byron’s Heavy Hitters Couldn’t Quite Get The Job Done
The Steel-type specialist and Canalave Gym Leader, Byron gives Ash a tough test, despite Ash thinking his Buizel and Chimchar would be able to capitalize on type advantages and earn an easy victory. Byron’s Bronzor reduces the damage received by Fire-type moves and even uses Rain Dance to reduce Chimchar’s attacks further.
Chimchar pulls through and defeats Bronzor and Steelix, but the damage is done and it falls to Bastiodon. With Ash’s Buizel falling earlier on to Steelix, Gliscor is called upon to pull out an unlikely victory over the bulky Bastiodon, but it succeeds with an impressive Fire Fang, earning Ash the Mine Badge.
6 Gardenia Wasn’t As Formidable In Their Rematch
Ash actually faces Gardenia in a normal battle before even realizing that she is the Eterna City Gym Leader, with her Turtwig easily sweeping through Ash’s Turtwig and Staravia after she reads the situation and quickly recalls her Cherubi.
By the time that Ash faces her in an official capacity, he has trained his Pokémon up considerably and is able to emerge victorious with the Forest Badge. Ash’s Staravia defeats Gardenia’s Cherubi before falling to her Turtwig, but Ash’s Turtwig is able to beat its counterpart. Gardenia has her final Pokémon, Roserade, use a Weather Ball with Fire-type properties, eliminating Turtwig and leaving it to face up against Aipom. Aipom is eventually able to rally and pick up the win for Ash, with its intelligence pushing it through to the end.
5 Roark Dealt Ash’s First Sinnoh Gym Defeat At The First Attempt
Despite Ash being able to witness his rival Paul defeat the Oreburgh Gym Leader, Roark, he is unable to pick up a victory himself in his first challenge against the Rock-type specialist. Roark’s Cranidos and Onix cause Ash problems with Cranidos tiring out Ash’s team, allowing Onix to pick them off.
Ash manages to win the rematch, but his task is made even harder with Roark’s Cranidos evolving into Rampardos during the short time between both their battles. Rampardos is now seen as the main standout threat to Ash’s team, but with his spinning dodge strategy, Ash’s Turtwig is able to defy the odds and pick up the win.
4 Candice’s Abomasnow Changed The Landscape Of The Battle Upon Its Introduction
Candice proves to be a formidable opponent for Ash to face in his Snowpoint Gym challenge, with her specializing in Ice-type Pokémon. Ash is able to get through most of the 4-on-4 bout relatively unscathed, defeating Sneasel, Medicham, and Snover while only losing Gliscor in return, but his fortunes change when Candice’s Abomasnow enters the fray.
Abomasnow instantly wrecks Staraptor and Grotle, but the spirited Chimchar is able to rally and overcome the overwhelming size difference by skating around on the ice and using its super-effective Fire-type moves in order to pick up the win and earn Ash the Icicle Badge.
3 A Win Over Dawn & A Draw With Ash Helped Maylene Find Her Fighting Spirit Again
Ash arrives in Veilstone City to challenge the Gym Leader Maylene, only to find her confidence shattered and the respect of her Lucario left wanting due to her humiliating loss to Ash’s rival Paul. Maylene is able to regain her fighting spirit by having a battle against Dawn, who also needs to find some inspiration, and she defeats the Pokémon Coordinator in a 3-on-3 bout, only losing her Meditite.
This warm-up match leaves her ready for Ash’s official Gym challenge, and this battle does not disappoint. With Maylene’s Machoke and Meditite and Ash’s Staravia and Chimchar eliminated, the final showdown is between Lucario and Buizel. The two have one of the best fights of the entire Diamond & Pearl series, ending in a double knockout and draw. Maylene still deems Ash’s performance worthy enough to award him the Cobble Badge, despite him not winning, showing shades of his Kanto campaign.
2 Fantina’s Drifblim Was A Frustrating Opponent For Ash To Overcome
Ash is initially made to wait for his Hearthome City Gym challenge when he discovers that the Gym Leader is off traveling somewhere, but he happens to run into Fantina while on the road. He loses a trainer battle with her due to her Drifloon evolving into Drifblim and causing all sorts of problems for his Pikachu, Buizel, and Chimchar, but he still manages to learn about her main strategies and tendencies.
When Ash gets his rematch at the Hearthome Gym, he uses an impressive strategy called the Counter Shield to avoid the effects of Hypnosis and is able to get past Gengar and Mismagius thanks to the efforts of Buizel and Chimchar respectively. However, Drifblim proves to be a tricky opponent once again, eliminating both Pikachu and Buizel, before eventually falling to Chimchar, earning Ash the Relic Badge.
1 Volkner Gave Ash An Electrifying Challenge
It takes an intense battle between Ash and Elite Four Member Flint to reignite the Sunyshore Gym Leader’s passion for Pokémon battling once again, but when he finally accepts Ash’s challenge, Volkner gives him an exciting battle.
Volkner immediately shocks Ash by countering the obvious type disadvantage that the Gym Leader’s Electivire has against Ash’s Torterra, with the Electric-type knowing and using Ice Punch to knock its opponent out. Pikachu and Infernape are able to defeat Electivire and Jolteon respectively, with the finale being Infernape against Luxray. Infernape wins thanks to activating and controlling its Blaze ability. Ash wins the Beacon Badge after an intense battle and is more than ready for the Pokémon League.
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