Your Hardest Gym Battle

As the title suggests, I’d like to hear about everyone’s hardest gym battle(s) when a gameboy was the only important thing in life.

I only played the games up to the second gen, but a vivid memory I have is when I first picked up Pokémon yellow and couldn’t get past Brock with my pikachu and butterfree (I was unaware of Nidoran and double kick!). I remember spending hours and hours training a party that were all useless against ground Pokémon. Pokemon blue / red is a breeze in comparison but I didn’t play these until after yellow.

In the second gen I still have nightmares about Whitney’s Miltank!


My hardest gym battle, is going to the gym after working an 8 hour day :face_with_spiral_eyes: but I get myself there no matter what!


@belch you hit the same ones I would have said off the bat! I also had yellow and my first playthrough I was also unaware of nidoran’s double kick which came in clutch in later replays. I also agree that Whitney’s miltank rollout and milk drink were the stuff of nightmares once it got rolling along.

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I recently played the original gold and heart gold, the Miltank rumors are real! That battle was ridiculous.

Also in heart gold playing red is pretty difficult as well. His Pokémon are much higher in level. That is the only part of the game I didn’t beat.


LOL Miltank! First plathrough she was annoying but still managed just fine. Second playthough and on shes cake. Just trade a drowzee or abra (depending on your version)to the man in goldenrod dept store for his machop. It’s bye bye Miltank from there. If I had to pick a gym leader it would be Blue. His team is balanced so unless you know his lineup and or have a good balanced team or really high leveled pokemon it can mess you over.

Wasn’t technically a Gym battle but the elite four in Black 2. It was the first game I had ever played and didn’t know about the run mechanics or the fact you could catch other Pokémon. I went through that entire game with just an Emboar… just proves how easy that game was if I didn’t really start having trouble until the Elite Four came around… I eventually learned you could catch Pokémon to beat them so I ended up beating them with a level 85 Emboar and 5 level 55 Pokémon from Victiry Road :wink:


It’s Miltank. It’s always been miltank. There are other battles that can potentially be tough, but given where most people are with their team in Gold/Silver/Crystal when they battle Whitney she is truly crazy tough.

I think the gym leader with Poliwrath can be tough too because he has that hypnosis, lock on, dynamic punch combo. Whitney was legit though lol


If I remember correctly there was a Glalie on Platinum maybe? My Torterra used to get crushed.

But nothing has, or ever will, compare to that stupid Miltank.

Honorable mention - choosing Charmander on Red, only using one Pokemon because you were 10, and enduring that entire cruise ship of x2 weakness.

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Brock and Whitney put hair on my chest.

Misty’s Starmie with Bubblebeam also gave me fits as a kid. Koga’s Muk using minimize should have been banned. Morty’s Gengar was a fierce beast to face when most of your Pokemon were just break into their 20s. Chuck manhandled me with his Poliwrath. Tate and Liza stomped me over and over again my first playthrough of Emerald.

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I remember miltank being difficult as well. Rollout was very powerful attack!

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I don’t remember which game it was, but I remember one of the gym leaders having a steelix that was very difficult for me to beat. It was definitely a older game. That iron tale attack would wipe my Pokémon out!

I didnt really have a hard time with the gym battles themselves. I would just level up a ton beforehand. I had more issues figuring out the stupid puzzles.

Probably Misty when I picked Charmander. Got rekt pretty hard.

It’s this reason that bulbasuar is my favorite gen 1 pokemon. Literally smash through the first 3 gym leaders and by the time you fight Erica there are a list of pokemon you could use at that point.

I have to agree with @smpratte … Red was a pain in the ass to beat. I also always remember ( the first time around ) Lance pissing me off in the Pokemon League. I remember beating Karen thinking I was done with the Elite Four and Lance showing up to fuck me up as almost all my Pokémons were paralyzed, poinsoned or asleep ;(

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Not a gym battle per se, but Cynthia in DP.

I wasn’t too into the games when I played Diamond so I thought I had done it when I took down the elite four, nope. Cynthia destroyed me the first time and I had to go back through again after stocking up on everything. Even then it was rough. But that’s how champion battles should be, I hated the Zinnia battle in ORAS where you just bring in your Mega Ray and OHKO her whole team.

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Whitney in Silver/Gold. It always takes me multiple attempts to beat that Milktank of her’s.

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Technically it’s not a gym battle, but you do get a gym badge so I’m counting it. The hardest battle in all the pokemon games is the last battle in the Pika Cup round 2 on Pokemon Stadium. If you don’t import any pokemon into the game it’s entirely luck based just beating them.

Brock with my Charmander in Red version, it was a nightmare grinding my charmander to lv16 in viridian forest just to kill that Onix. Meanwhile, my neighbour was annoying me with how his Squirtle clearing Brock in 1 battle :unamused: