What gym leaders have you struggled against before?

My Rock monotype vs Gardenia kinda sucked

There was one playthrough of Soul Silver where Chuck kinda beat my ass cuz my team was a little underpowered and iirc not particularly well-suited to handling him, made all the worse by Johto's level curve/poor grinding ability
 
I usually only struggle against early game Gym Leaders if I have the wrong type starter for it and have not had a chance yet to catch something strong against them.
For example fighting Falkner with a Chikorita is a pain lol

Can't really think of any Gym Leaders that are always a struggle. It always depends heavily on the team you put together.
I'd say Double Battle Gym leaders tend to be tougher, such as Tate and Liza or Raihan.

Idk why people struggle against Whitney. The times I fought her always went smooth enough >.>
 
Seems like Totem Wishiwashi was tough initially. Called out Alomomola first. Crushed Fomantis with a Helping Hand Water Gun. Brought Torracat and Cutiefly besides that. (Sticks with new Pokemon on first playthroughs.) Probably tried to paralyze it. Cleansed that with Alomomola's Healer ability. Won thanks to item spamming and perhaps Struggle Bug?

Wiped to Totem Marowak in a blind Nuzlocke. Trusted Brionne to do better. Cannot recall the rest of the team. (Bets on Mudbray or another Ground-type. Expected Salazzle still.) Won the rematch with Gyarados. (Dislikes Gyarados. Already had a Water type too.)
 
i have vivid memories of struggling against all of the hoenn gym leaders the first time i played the game and honestly they can still be challenging at times, i find them the hardest group of gym leaders, looking at the regions as a whole. lots of struggles against misty, morty, chuck, claire...fantina in DP specifically. oh cheren in BW2 is rough lol even to this day. like that, to me, is the most difficult first gym leader. totem wishiwashi is a pain too.
 
Certain totem pokemons are biggest struggle yet especially if the totem summons a ally that benefit it and the ally. Quite remember I have hard time with wishwashi and lurnatis one-shot everything with physical solar-beam (can't remember the name)

Early gym, might put you in a tough pickle like when you go with a charmander few gyms isn't easy and metal claw do bit some damage to brock's pokemon. The whiney always gives me a hard time because of notriously using roll out with milk drink and attract.. Having Cynaquil was a bad idea to go against it because thick fat making it hard to use with STAB moves
 
I remember a few Gyms being a challenge in earlier gens but still not too hard. I'll just list them all by their region:

- Sabrina in Kanto, maybe even Misty sometimes depending on my team at the time
- In Johto it all depends on the team I have at the time of each battle but leaders like Whitney, Morty and Jasmine were all challenging at some point, especially Morty if he kept hitting every Hypnosis attack since I don't like using healing items in battles
- Hoenn was only challenging in OG Gen 3 and the leaders that could be tough to beat imo were Brawly, Wattson and the toughest one being Winona and her Altaria
- In Sinnoh I never had any issues with any of the Gym leaders but if I had to pick one then I'll go with Roark since Cranidos has huge attack and Headbutt from it could be a problem depending on your team
- The last region with challenging Gym leaders was Unova imo but even Unova didn't have that many challenging ones tbh. The three I would point out are Elesa, Cheren and Lenora since all three can be challenging depending on you team and it's levels
 
I struggled in my very first gen 1 playthrough against Brock because my starter was Charmander and Kanto was basically designed to screw on Fire types. A Butterfree with Confusion ended up taking out the gym. Whitney's Miltank also gave me some troubles since I didn't have anything strong for it. Clair's Kingdra with her Dragonairs using Thunder Wave and Kingdra having basically no weaknesses was kinda tough as well.

Unfortunately, the big majority of gym leaders in the franchise weren't any memorable. I even forgot what team many of them had as I probably spent more time solving the gym puzzle than fighting them. I think Platinum, and BW2 (challenge mode) had the most compelling and properly balanced gyms overall.

But to be fair, it's been a few years since I started playing on Battle: Set mode, when I was a kid I allways played with free switches and didn't even pay attention to levels so sometimes I was overlevelled. Nowadays I allways play with a set of self-imposed rules: No overlevelling, no using more Pokémon than the leader, no using items even if the AI does, and no legendaries. I also ban pseudo-legendaries and broken megas from my playthroughs depending on the game, the only pseudo I don't ban is Tyranitar because its typing sucks so it compensates.
 
Zed01 said:
- In Sinnoh I never had any issues with any of the Gym leaders but if I had to pick one then I'll go with Roark since Cranidos has huge attack and Headbutt from it could be a problem depending on your team
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Yeah, I remember struggling against him, even lost a couple of times when I chose Piplup or Turtwig (before they gained a few levels and evolved). Not having a 4x water or grass weakness like Brock made it a bit harder, and Cranidos actually hit more aha.

Gardenia was also a bit tough for me at first, same with some of the other Sinnoh gym leaders in my first few runs until I leveled up more. I found the earlier Sinnoh gyms tougher than most of the other main series games (save for Whitney and Morty, mostly in GSC).
 
Growing up I had trouble with Brock (chose charmander), Whitney, Clair, Wattson, sometimes Winona, and Fantina (Platinum). Out of those gym leaders the only one that has stayed a consistent pain in the ass is Clair. Whenever I get to Blackthorn city I'm always under leveled and it's rare I have an ice or dragon type on my team in those games to counter her.
 
i don't recall having issues with any gym leaders :c they weren't really all that hard, but i was always the type to overlevel, so...

if we're counting totem battles though, totem lurantis was awful. ;_; struggled against that one for sure!
 
When I was a kid I had a hard time against Flannery, specifically in Saphire. I always took Torchic and never was that prepared for her and that Overheating Torkoal would demolish me. I had a tough time with a lot of the gen 3 leaders back in the day though. I remember wiping to Brawly and Norman a few times as well. Not sure how considering I always used Taillow...
 
Figure said:
When I was a kid I had a hard time against Flannery, specifically in Saphire. I always took Torchic and never was that prepared for her and that Overheating Torkoal would demolish me. I had a tough time with a lot of the gen 3 leaders back in the day though. I remember wiping to Brawly and Norman a few times as well. Not sure how considering I always used Taillow...
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Same! I lost to her fairly often if I wasn't using Mudkip as my starter, the Overheat was tough. Tate & Liza were pretty brutal too. Norman also, and occasionally Wattson depending on who I was using.. so basically Hoenn haha.
 
Figure said:
When I was a kid I had a hard time against Flannery, specifically in Saphire. I always took Torchic and never was that prepared for her and that Overheating Torkoal would demolish me. I had a tough time with a lot of the gen 3 leaders back in the day though. I remember wiping to Brawly and Norman a few times as well. Not sure how considering I always used Taillow...
Click to expand...

Woah, you're literally me or something? I used to always pick torchic and taillow as my bird lol. Honestly I had a bunch of trouble with the 8th gym because my electric type would be manectric and it didn't do well against that kingdra. Granted, I was like 5 back then
 
Clair in SoulSilver
Crasher Wake in Platinum. I relied on Infernape so this was very hard.
Cheren, Elesa, Skyla, and Marlon in Black 2. Maybe my team was bad since I also struggled against the Elite Four.
Kiawe and Mallow in Ultra Moon
 
I lost to Burgh in my playthrough of B2 a few months ago.
The enemy Pokémon's levels are quite a bit high early on.
 
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