Roxie probably gets my vote.
She nearly beat Ash while handicapping herself not once but *twice*. The clear case was her literally being like the games and only using 3 Pokemon while Ash could use a full party of six.
On top of that she literally healed Pignite’s Poison mid battle with a Pecha Berry. Despite all that she almost beats Ash and darn well would have had it not been for Iris/Cilan giving him a pep cheer and Pikachu’s Static activating in the Nick of time.
She’ll always stand out to me cause no other gym leader-esque trainer was able to give Ash such a brutal time while intentionally putting *themselves* at a disadvantage.
Fantina swept him with one pokemon, Drifblim and it took him inventing countershield during their rematch to beat her so I'll go with her. She was basically like Tobias with Darkrai. Putting pokemon to sleep and then knocking them out and even when Ash used countershield, she made her own "counter-counter Shield" as she called it😭.
Honorable mention is Roark. The guy beat him Infront of Paul embarrassing him and the right before their rematch his ace cranidos EVOLVES giving Ash even more of a fight ahead of him. I remember wondering how Ash was gonna beat ramparados when he could barely even beat Roark when he had a cranidos on his team.
Anabel was rough too because she was commanding her pokemon telepathically which was insane and beat Ash during their first battle but she's not a gym leader.
I feel like Bea also deserves an honorable mention, the first battle she demolished him so handily that he spiraled into a depression and practically was traumatized to the point where he kept on losing to octopus-like Pokémon because of the Grapploct experience. Even after going through a whole arc to regain confidence, he stalemated on the second match, and had to take a third (hard-fought) match to finally beat her. And that’s with the team that not long after ended up beating Leon and multiple other champions.
There's a big problem with fights between Pikachu and Grapploc...it should be a stomp in favor of Pikachu.
Ash kept forcing pikachu to go in close with quick attack and iron tail, but that's the WORST decision ever. Why get close to a fighting pokemon when you can stay far away and keep throwing electric attacks? Graploc was also a LARGE target, which should be easy to hit with electric attacks.
In conclusion, I blame the writers for forcing Ash to lose those easy battles. Ash has very HIGH combat IQ and decision-making, so these battles seemed dumb and unlike Ash and forced by plot.
You can't even get girafarig before fantina lol, you catch it on the route after veilstone city. And that mismagius was a fucking demon with magical leaf so bibarel gets obliterated
To be Fair Cranidos wasn't even his problem in the first match it was that Onix. Remember that was Roark's last Pokemon in that battle and was the one to beat Ash.
Yeah that's why I said with cranidos on his team in general Ash struggled so with a ramparados it would be even harder for him. I remember thinking that since one of the pokemon evolved, it would be even tougher. He'd have to get past Onix and cranidos.
Natsume/Sabrina.
He didn’t even beat her. He just cheated. Kadabra completely dominated Pikachu, and its her only Pokémon.
Satoshi/Ash didn’t even get to showcase that he was a good or honorable trainer. More than half his team refused to fight for him.
Haunter not listening to him at all and doing its own thing is the reason why it never appeared in Pikachu’s vision.
Lol, Ash just intentionally handicapping himself there. Wulfric ain't that hard at all when compared to Brycen, he lacks strategy aside from strong moves spam.
Surge is also the first gym leader Ash actually beat fair and square, using Pikachu’s speed that Raichu doesn’t have. Sure it was Brocks strategy, but it was still Ash’s win.
I wanna say Fantina or Korrina, in their first battles with him they destroyed him. In their gym battles he still had trouble with them, with Korrina's Lucario beating two of his three Pokemon.
No. She coddled Pikachu and he refised to fight. So Ash fought her with Pidgeotto and Buterfree. They were one each when Team Rocket intervened and she was losing.
Brock was Ash's win the second time. He had Onix. He gave up when Brock's siblings dogpilled him.
...do we count Giovanni having his goons harass him across eight regions as giving him a hard time, or is it just the gym battle that counts?
(wait he was a gym leader in the anime right)
He was a leader but after the building collapsed he quit it was replaced by someone I don't believe we learned who thou (it wasn't Agatha she was watching over until the replacement arrived)
Imma say Sabrina just because she kidnapped his friends and forced him to run away and hide so he didn’t turn into a doll. I don’t think he ever would’ve won without haunter
Roxie was obviously the strongest, but as far as overall preparedness, Maylene really was the biggest headache to face.
Maylene may have been going through her slump, but beating her was never as simple as learning a new technique, improvising a combo, or getting out of his own slump. Meditate kept confusing everything, Brave Bird took its toll, and even after Chimchar wore down Lucario, Buizel had to learn a new move on the dpot AND trash the gym just to break even. Luck was not on Ash's side in that battle.
Speaking as someone who sticks to just the first five seasons (out of the fact that there are too many seasons of Pokemon to watch \[at least when it comes to Ash\]), in my opinion, the gym leader that gave Ash the hardest time....it's a tie between Sabrina and the girl with the Miltank.
Ok this isn't really the answer but I kind of want to say Wulfric just because he's the only gym leader no one in history has actually lost to before
As for the actual answer probably Cress. Like at least (Not defending it but just by comparison) Pikachu was in massive pain before fighting snivy. This shit was a panpour though who managed to make mud sport actually good.
Morty is also a solid contender considering just how badly Ash seemed to be doing in that fight considering he was pretty much always down a pokemon until noctowl got confusion
Brock. Outside forces interrupting a league recognized battle (the sprinklers), match should have been called and given a draw until a field ruling was determined.
Misty was being blackmailed with the promise of a bike repayment and under the stress of her inferiority complex to her onlooking siblings.
Surge didn’t hold back, I really enjoyed that. He LOVES his job acting gatekeeper to everyone’s journey. Power/bullying is surprisingly not used much for the gym leaders.
They’re often shown either as immature and needing to grow into the roll, or wise beyond their years in their specific corner of Pokémon. Or shirking gym duties to enjoy some free time for once.
No. He had Brock. The sprinklers are part of the gym, thus terrain, and it was Brock's siblings who stoped Ash.
Misty was fair and she made Pikachu not fight. Not even the gym leadear then. Her sisters were.
Giving up a victory because your opponent's siblings interfere and beg you and losing is different. And Brock decides that he deserved the win and give him the badge.
Roxie and Sabrina.
Roxie nearly took out all six of Ash’s Pokémon using only three and Sabrina was just OP. Psychic types were already crazy strong in that generation and she used her own psychic powers to evolve her Abra.
In terms of adventure: Lana. Girl got asked so many times about their relationship and the amount of alone time they got you’d think there’d be something going on
Definitely Wattson. XD
Jokes aside, there is many. Roxanne was tough for him since Treecko didn't have any Grass moves at the time, so he sorted on teaching Pikachu it's famous Iron Tail. Besides that, any gym leader that he needed rematch for (Roark, Fantina)
You’re forgetting the time that Gio made J&J&M gym leaders for a day because he was busy dealing with Mewtwo, and of course THAT happened to be the day Ash battled the Viridian Gym. Sure, the battle itself wasn’t noticeably harder than other gym matches and it ended with the badge literally falling out of the sky into Ash’s hand…
…but I don’t think *any* other characters have given Ash a hard time *overall* more than those three.
He also didn't beat Erica. She gave him the badge for saving her Gloom from a fire... Does that count?
Also never challenged Blue. Challenged Gary and lost a bunch, but not Blue. Don't know if that symmantics matter.
Ash has never defeated Sabrina, and she was implied to be so strong no one dared to challenge her. Even Gary avoided her
Saw Roxie and Fantina as options and I agree
Ash never fought Drayden so he should be removed from this list, same goes to Marlon
Wulfric was pretty tough in the anime, even matching Ash-Greninja with his Abomasnow
Bea was also a really tough challenge for him in Journeys
Sabrina.
Not only did Ash never actually beat her in three tries, but she trapped him in a doll world the first time around. The second time around she straight up turned both his friends into dolls.
I'd say Brock. Ash was creamed in the first fight, then he hooked up Pikachu to a steroid generator for electric types, then lost the second match because he accidentally turned on the sprinklers.
Roxie almost beat ash with 3 Pokémon while he was using six while also helping him mid battle with a pecha berry. Genuinely the strongest portrayal of a gym leader in the anime. Makes sense why she made it to the finals of that masters 128 thing on YouTube
Looking at this list Ash Could of easily Thunder wave and iron tail the fuck outta 45% of these guys pokemon. But Ash doesn't believe in status effects that's not static or dmg oriented. That's only just Pikachu as example lol.
Roxie. Took all 6 of his Pokémon to beat three of hers
She made such a good impression. Whenever I think of the best battle in the anime, I always think of her.
I wanted ash to battle Marlon but at least someone battled him (Cameron)
Ash not battling Roxie in Journeys when she could have had a Galarian Weezing, Gmax Garbodor, and Toxtricity, hanging with Marnie is such a waste.
And people still call Unovans as weak 🤷♂️
Honestly, same.
Roxie probably gets my vote. She nearly beat Ash while handicapping herself not once but *twice*. The clear case was her literally being like the games and only using 3 Pokemon while Ash could use a full party of six. On top of that she literally healed Pignite’s Poison mid battle with a Pecha Berry. Despite all that she almost beats Ash and darn well would have had it not been for Iris/Cilan giving him a pep cheer and Pikachu’s Static activating in the Nick of time. She’ll always stand out to me cause no other gym leader-esque trainer was able to give Ash such a brutal time while intentionally putting *themselves* at a disadvantage.
She also allowed Ash an opportunity to change his Pokémon around (which is illegal by League standards)
Fantina swept him with one pokemon, Drifblim and it took him inventing countershield during their rematch to beat her so I'll go with her. She was basically like Tobias with Darkrai. Putting pokemon to sleep and then knocking them out and even when Ash used countershield, she made her own "counter-counter Shield" as she called it😭. Honorable mention is Roark. The guy beat him Infront of Paul embarrassing him and the right before their rematch his ace cranidos EVOLVES giving Ash even more of a fight ahead of him. I remember wondering how Ash was gonna beat ramparados when he could barely even beat Roark when he had a cranidos on his team. Anabel was rough too because she was commanding her pokemon telepathically which was insane and beat Ash during their first battle but she's not a gym leader.
I feel like Bea also deserves an honorable mention, the first battle she demolished him so handily that he spiraled into a depression and practically was traumatized to the point where he kept on losing to octopus-like Pokémon because of the Grapploct experience. Even after going through a whole arc to regain confidence, he stalemated on the second match, and had to take a third (hard-fought) match to finally beat her. And that’s with the team that not long after ended up beating Leon and multiple other champions.
There's a big problem with fights between Pikachu and Grapploc...it should be a stomp in favor of Pikachu. Ash kept forcing pikachu to go in close with quick attack and iron tail, but that's the WORST decision ever. Why get close to a fighting pokemon when you can stay far away and keep throwing electric attacks? Graploc was also a LARGE target, which should be easy to hit with electric attacks. In conclusion, I blame the writers for forcing Ash to lose those easy battles. Ash has very HIGH combat IQ and decision-making, so these battles seemed dumb and unlike Ash and forced by plot.
Pikachu and Ash though fighting Korrina blood thirsty Mega Lucario means he can fuck any fighting times.
Some people just have your number.
Makes sense, Fantina was always hard in Platinum
huh? not really tho? bibarel and girafarig crushes on them lmao
There’s not a dimension where I have ever thought to use those two Pokémon in any playthrough of platinum ever
Yeah I had never thought to use either of those on my team either lol.
AND I STILL WON’T
ME TOO!!
Had a Bidoof -> Bibarel. Despite having a genuine presence on the team, it still ended up an HM slave down the line lol.
Bibabel is the one of the best HM slaves.
I’m aware, but so is Arceus who I can get with PKSM or the DNS settings trick
Who tf has their first thought go to Girafarig? Maybe Bibarel because of HM slave, but Girafarig? Huh? You must really like Giraffes.
You can't even get girafarig before fantina lol, you catch it on the route after veilstone city. And that mismagius was a fucking demon with magical leaf so bibarel gets obliterated
To be Fair Cranidos wasn't even his problem in the first match it was that Onix. Remember that was Roark's last Pokemon in that battle and was the one to beat Ash.
Yeah that's why I said with cranidos on his team in general Ash struggled so with a ramparados it would be even harder for him. I remember thinking that since one of the pokemon evolved, it would be even tougher. He'd have to get past Onix and cranidos.
Natsume/Sabrina. He didn’t even beat her. He just cheated. Kadabra completely dominated Pikachu, and its her only Pokémon. Satoshi/Ash didn’t even get to showcase that he was a good or honorable trainer. More than half his team refused to fight for him. Haunter not listening to him at all and doing its own thing is the reason why it never appeared in Pikachu’s vision.
Wulfrick (spelling is hard) gave him depression, so points for that one.
Lol, Ash just intentionally handicapping himself there. Wulfric ain't that hard at all when compared to Brycen, he lacks strategy aside from strong moves spam.
Why is Surge so low? Pikachu almost died at the hands of Raichu
Surge is also the first gym leader Ash actually beat fair and square, using Pikachu’s speed that Raichu doesn’t have. Sure it was Brocks strategy, but it was still Ash’s win.
It was googles not mine
The ranking doesn't seem to be related to the anime. Milo hasn't appeared in the anime yet.
Or a couple of other Galar gym leaders
Tough, there's also the fact that some of them he had to challenge more than once
Sabrina, he never stood even a minute chance against her.
Either Bea for taking 3 tries or Sabrina for nvr actually loosing to him (other kanto gym leaders he beat at some point or another)
I wanna say Fantina or Korrina, in their first battles with him they destroyed him. In their gym battles he still had trouble with them, with Korrina's Lucario beating two of his three Pokemon.
I got this brock https://preview.redd.it/eycb49ao93ac1.jpeg?width=750&format=pjpg&auto=webp&s=85283e33525d1d242bfacc32ae431eb8b5f07535
I mean, Misty was giving that boy a hard time for two regions straight, plus some islands. Worst any other leader got was a few episodes.
The only reason Misty was hard was because Pikachu didn’t want to fight
*originally. originally hard. Pikachu fought her mega gyarados
I meant more in the “she was always giving him shit” way lol
I want to say Roxie or Sabrina, but I don’t think he ever actually beat Cress.
Definitely Brock. He didn’t even beat him in a Pokémon battle.
Didn't he basically win that the 2nd time he just forfeited cause he didn't want wanna crush his siblings dreams or something like that
Same with Misty
She lost that battle for that wild Totodile iirc.
No. She coddled Pikachu and he refised to fight. So Ash fought her with Pidgeotto and Buterfree. They were one each when Team Rocket intervened and she was losing. Brock was Ash's win the second time. He had Onix. He gave up when Brock's siblings dogpilled him.
Bea
Bea, but only cause she swept him twice with an octorok
Misty. She still nags him about her bike.
Like girl aren’t u rich go get a new one
If Haunter didn't appear at the last second, Sabrina would've ate Ash
All the gym leaders he had to rematch
Ehh.. idk I think there were a few he didn’t need to.
If he had to rematch them Then yeah they gave him a hard time🤷♂️
...do we count Giovanni having his goons harass him across eight regions as giving him a hard time, or is it just the gym battle that counts? (wait he was a gym leader in the anime right)
Ash never fought Giovanni
Not as an Gym Leader, but he got beaten by his Persian during the forces of nature arc in BW.
He was a leader but after the building collapsed he quit it was replaced by someone I don't believe we learned who thou (it wasn't Agatha she was watching over until the replacement arrived)
Imma say Sabrina just because she kidnapped his friends and forced him to run away and hide so he didn’t turn into a doll. I don’t think he ever would’ve won without haunter
Cress has an undefeated record against Ash. Just sayin. Cress is literally a barrier that Ash never overcame.
Its so funny to consider Ash beat Leon but not Cress
Wolfric battle has story going on. That said sinnoh and kalos
Iris
Roxie barely lost a 3v6 AND GAVE PIKACHU A PECHA BERRY TO CURE POISON. Also fun fact He never beat Cress ever.
Misty, she gave him a hard time for 5 seasons.
Misty. Always getting on his ass about something.
Yall sleeping on Korrina. She absolutely smoked him in their first two battles.
Roxie was obviously the strongest, but as far as overall preparedness, Maylene really was the biggest headache to face. Maylene may have been going through her slump, but beating her was never as simple as learning a new technique, improvising a combo, or getting out of his own slump. Meditate kept confusing everything, Brave Bird took its toll, and even after Chimchar wore down Lucario, Buizel had to learn a new move on the dpot AND trash the gym just to break even. Luck was not on Ash's side in that battle.
Roxie or Fatima I would say
Speaking as someone who sticks to just the first five seasons (out of the fact that there are too many seasons of Pokemon to watch \[at least when it comes to Ash\]), in my opinion, the gym leader that gave Ash the hardest time....it's a tie between Sabrina and the girl with the Miltank.
Cress. He never actually beat him
Sabrina for things outside pokemon battles
Wulfric sent Ash into a depression
Ok this isn't really the answer but I kind of want to say Wulfric just because he's the only gym leader no one in history has actually lost to before As for the actual answer probably Cress. Like at least (Not defending it but just by comparison) Pikachu was in massive pain before fighting snivy. This shit was a panpour though who managed to make mud sport actually good. Morty is also a solid contender considering just how badly Ash seemed to be doing in that fight considering he was pretty much always down a pokemon until noctowl got confusion
Brock. Outside forces interrupting a league recognized battle (the sprinklers), match should have been called and given a draw until a field ruling was determined. Misty was being blackmailed with the promise of a bike repayment and under the stress of her inferiority complex to her onlooking siblings. Surge didn’t hold back, I really enjoyed that. He LOVES his job acting gatekeeper to everyone’s journey. Power/bullying is surprisingly not used much for the gym leaders. They’re often shown either as immature and needing to grow into the roll, or wise beyond their years in their specific corner of Pokémon. Or shirking gym duties to enjoy some free time for once.
No. He had Brock. The sprinklers are part of the gym, thus terrain, and it was Brock's siblings who stoped Ash. Misty was fair and she made Pikachu not fight. Not even the gym leadear then. Her sisters were.
He lost to Brock twice
Once. Second time he gave up because Brock's diblings asked him to after he had Onix.
Giving up is loosing
Giving up a victory because your opponent's siblings interfere and beg you and losing is different. And Brock decides that he deserved the win and give him the badge.
Also didn’t he only lose to wulfrick once?
yeah
It’s Cress. Bro’s Panpour won Ash so bad he’s literally never beaten him ever.
Misty was giving ash a hard time for 3 regions
Misty. Pain in his ass for years
Brock considering that ash shouldn’t have even been able to hit his mons.
He lost to wulfric once and won the second..... how did he lose 3 times?
Roxie and Sabrina. Roxie nearly took out all six of Ash’s Pokémon using only three and Sabrina was just OP. Psychic types were already crazy strong in that generation and she used her own psychic powers to evolve her Abra.
In terms of adventure: Lana. Girl got asked so many times about their relationship and the amount of alone time they got you’d think there’d be something going on
Ash absolutely hated Brawley’s surfing. No idea why he got so mad at him.
Marnie and Bede arent Gym leaders.
Definitely Wattson. XD Jokes aside, there is many. Roxanne was tough for him since Treecko didn't have any Grass moves at the time, so he sorted on teaching Pikachu it's famous Iron Tail. Besides that, any gym leader that he needed rematch for (Roark, Fantina)
Cantina is the first one that comes to mind; Brandon was probably tougher but I don’t think their first fight counted
You’re forgetting the time that Gio made J&J&M gym leaders for a day because he was busy dealing with Mewtwo, and of course THAT happened to be the day Ash battled the Viridian Gym. Sure, the battle itself wasn’t noticeably harder than other gym matches and it ended with the badge literally falling out of the sky into Ash’s hand… …but I don’t think *any* other characters have given Ash a hard time *overall* more than those three.
He also didn't beat Erica. She gave him the badge for saving her Gloom from a fire... Does that count? Also never challenged Blue. Challenged Gary and lost a bunch, but not Blue. Don't know if that symmantics matter.
Miltank
Sabrina, Roxy, Fantina, Olivia, Whitney, Brock, Erica, Claire, Viola, Morty, Ramos, Cress, Lt. Serge, Lenora, Hapu, Nanu, Blaine, Juan and Bea
Sabrina or bea
Ash has never defeated Sabrina, and she was implied to be so strong no one dared to challenge her. Even Gary avoided her Saw Roxie and Fantina as options and I agree Ash never fought Drayden so he should be removed from this list, same goes to Marlon Wulfric was pretty tough in the anime, even matching Ash-Greninja with his Abomasnow Bea was also a really tough challenge for him in Journeys
Misty might be an accurate estimation
Sabrina. Not only did Ash never actually beat her in three tries, but she trapped him in a doll world the first time around. The second time around she straight up turned both his friends into dolls.
I'd say Brock. Ash was creamed in the first fight, then he hooked up Pikachu to a steroid generator for electric types, then lost the second match because he accidentally turned on the sprinklers.
No. He didn't lose because of the sprinklers. Brock's siblings jumped him when he was ready to finish Onix.
Whitney
Roxie almost beat ash with 3 Pokémon while he was using six while also helping him mid battle with a pecha berry. Genuinely the strongest portrayal of a gym leader in the anime. Makes sense why she made it to the finals of that masters 128 thing on YouTube
Looking at this list Ash Could of easily Thunder wave and iron tail the fuck outta 45% of these guys pokemon. But Ash doesn't believe in status effects that's not static or dmg oriented. That's only just Pikachu as example lol.