Most difficult Gym Leader battles

[Six Trails]

Whitney and her Miltank is objectively the hardest Gym Leader battle, but what other Gym Leaders did you find difficult to defeat or needed more than one try to defeat? In my opinion:

Whitney - Due to it's good speed and good bulk, it was hard to take out Whitney's Miltank because of Rollout which usually got continuously stronger to the point it's able to one-shot anything you send out. The only way to beat this thing besides leveling-up or lucking out with Rollout missing is to put it to sleep, and Sleep Powder's accuracy isn't the best.

Morty - Another invincible Pokemon, Gengar, is impossible to take out due to it's high speed, and the fact that it like never misses with Hypnosis. I swear that's the only way to beat it. It puts you to sleep and uses Dream Eater to recover from any damage previously inflicted on it. It's high Special Attack stat only makes it worse.

Jasmine - Mainly her Steelix. Bulky, especially given the fact that steel had so many resistances back in Gen II/IV. Her pesky Magnemites also always paralyzed my Pokemon also.

Clair - The typing overall (Dragon) also had a lot of resistances, including the type of each starter. Her Dragonair's ability to paralyze your Pokemon made it even worse.

Sabrina (Pokémon Yellow) - Most of the Gym Leaders in Yellow seemed to have over-leveled Pokemon for seemingly no reason. Since in Gen I Special Attack and Special Defense were the same, her Alakazam was even harder to take out, on top of the fact that it had Recover and it only had one weakness, Bug, which in Gen 1, most Bug Pokemon were relatively weak, AND there were only 4 Bug Type moves, and the strongest one had 25 Base Power.

 

[Kyo]

Man, I should get to replaying some of these since I remember almost nothing.

Off the top of my head, I seem to recall that in Emerald, which was a pretty easy game otherwise, Brawly was a bit difficult to take out in comparison due to his Makuhita, what with his Bulk Up + Reversal set.

 

[Captain Cadaver]

Brock and Misty were somewhat challenging if you started out with a Charmander in Gen 1, due to not being able to catch any Grass/Water types until just after them. Gen 3 made the first one far easier though by giving Charmander Metal Claw.

Other than that, the only Gym Leader I remember having trouble with was Lenora in Black/White, purely because of her Watchog being a Hypnosis troll.

 

[Pyro]

I remember having to redo the Miltank battle several times because Rollout was such BS. I think I leveled up and just took the motherfucker out right away.

I don't really remember tough battles though. Mostly because I was always grinding like Vegeta to level up and be far stronger than my opponents.

 

[Super Saiyan Overlord1007]

Whitney - Obvious reasons. Fucking cow and damn her Miltank too!!

(Morty & Jasmine weren't really problems for me)

Claire - I remember my mom, sister, and I rotated and took turns everytime we lost to her. We always got out asses kick before I somehow beat her.

Johto Elite Four

Lance (Champion) - Prior to actually beating him the best I managed to do was beat half of his team. Until I learned the secret of beating the Elite Four & Champion......Buy Full Restores, Hyper Potions, Full Heals, & Revives.

Wionna - I'm convinced that particular Altaria was haxed when I first played it.

Tate & Liza - Solrock & Lunatone were durable as Hell, in addition to being Rock Types, having movies like Flamethrower, Ice Beam, & Solarbeam. Lunatone having Recover and both raising their special stats. Even today they're still a pain in my ass.

Juan/Wallace - His water Pokémon are no problem, Milotic was the problem however.

Cynthia - Garchomp was a sweeper

Red - ....................

The others were more fun than challenging which is only half of the fun.

 

[Six Trails]

Wionna - I'm convinced that particular Altaria was haxed when I first played it.

Tate & Liza - Solrock & Lunatone were durable as Hell, in addition to being Rock Types, having movies like Flamethrower, Ice Beam, & Solarbeam. Lunatone having Recover and both raising their special stats. Even today they're still a pain in my ass.

Juan/Wallace - His water Pokémon are no problem, Milotic was the problem however.

I was thinking mainly of my first Gold play through when making the OP, so I forgot about a lot of the difficult leaders in Hoenn, but I have to agree these were difficult too, and Brawly like Kyo said.

Especially Juan for me, since back when I was like 7/8/9/whatever age I was when I first played, I only ever used my starter (Swampert) and everyone else on my team was either an HM hoe or someone I though looked cool or some random legendary with no EV investment. I wasn't very effective against Juan and he always wore down my Swampert with his team leaving me with like level 10 Zigzagoons.

Tate & Liza - Mainly the reason you posted, those things don't go down and didn't they have Recover also?

 

[Event Horizon]

Whitney's Miltank and her Rollout was god awful the first time I played through Gold and Silver. Nowadays, she's not nearly as big a problem to me. But the challenge was real back in the day.

Juan from Emerald can be a nightmare to face. That annoying ass Kingdra of his who spams Double Team and when you finally get its health low, it uses Rest and gets all of its health back. Not to mention it holds a Chesto Berry, so its first Rest is a free full restore.

Other than that, I didn't have too much difficulty with any other Gym leader.

 

[Six Trails]

I'm surprised no one else went for a Gym Leader from Yellow.

Compare the R/B/G Leaders' teams to the Yellow Leaders' teams.

 

[Papasmurf]

Clair and Sabrina are the only gym leaders I remember having much trouble with from the first 4 generations. Elesa gave me a teensy bit of trouble too, I believe.

 

[Kyo]

I'd completely forgotten about Juan from Emerald, and yeah he was a bit difficult as well. However I don't recall having much trouble with Winona or Tate/Liza. I do remember having a lot of trouble taking out Norman during my first run, though I think that was more due to me sucking than anything else.

I think between the two Dragon users, Clair was more difficult than Lance. Mainly because half of Lance's team weren't even Dragon types, and only 2 of his Pokemon had Thunder Wave while 3 (out of 4) of Clair's did (in G/S/C anyway). Not that that isn't troublesome as all hell, but significantly less so, plus iirc at this point in the game you could get Full Restores for the first time which made things a lot easier. Not to mention, apart from his Level 50 Dragonite, I don't think his Pokemon were too high-leveled for that portion of the story. But in any case, yeah, I do recall having trouble with both.

 

[Six Trails]

I also struggled with Norman. At that point in the game most Pokemon are what? High 20s at best? No one's really hit their third stage evolution and can't really do much damage to Slaking due to it's ridiculously high HP and good Defense. Coupled with it's high Attack and the STAB it gets on Facade, it can pretty much one-shot most of your Pokemon.

 

[Yoshi]

I'm surprised no one else went for a Gym Leader from Yellow.

Compare the R/B/G Leaders' teams to the Yellow Leaders' teams.

Yeah, going up against Brock with a Pikachu if you don't have Mankey, Butterfree, or one of the Nidorans is suicide.

 

[Kyo]

I also struggled with Norman. At that point in the game most Pokemon are what? High 20s at best? No one's really hit their third stage evolution and can't really do much damage to Slaking due to it's ridiculously high HP and good Defense. Coupled with it's high Attack and the STAB it gets on Facade, it can pretty much one-shot most of your Pokemon.

That is true. I'd have to replay to make sure. I assumed that it wasn't meant to be as bad as it was for me due to Slaking's troublesome (for him) ability, but I could be wrong there.

 

[Papasmurf]

I always usually trained my Combusken up to a Blaziken before facing Norman and won

 

[Six Trails]

Not exactly related to that Gym, but that's what I had to do when facing Morty the first time I played Gold. I had to get my Bayleef to a Meganium and have an 11 level advantage just to beat Gengar.

 

[withheldforprivacy]

1. Brock and Misty were somewhat challenging if you started out with a Charmander in Gen 1, due to not being able to catch any Grass/Water types until just after them.
2. Gen 3 made the first one far easier though by giving Charmander Metal Claw.

1. Pikachu, Oddish, Bellsprout (you can go to Bill's cottage before fighting Misty).
2. Gen 3 Brock has rock attacks, which makes him harder than his Gen 1 self, who has only lame attacks.

 

[Captain Cadaver]

Clair and Sabrina are the only gym leaders I remember having much trouble with from the first 4 generations. Elesa gave me a teensy bit of trouble too, I believe.

I'd almost forgotten about Elesa. Had to face her multiple times and overlevel my team a bit to beat her without wasting money on tons of potions.

 

[Pyro]

I played Yellow a few times (never all the way through since I was borrowing it), but I much preferred Red, so I didn't have to deal with any of the Yellow-exclusive problems you folks are bringing up.

 

[Doctor Havoc]

just Whitney was difficult, other leaders were mostly easily with a few giving a small challenge imo

 

[SSJ2]

Whitney was only really difficult for me when I chose Cyndaquil.