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Hardest battle you've had in any Pokemon game?

FireRed. Lorelei. This was years ago, but I had such a difficult time battling Lorelei the first time I played FireRed. I lost to her numerous times before I got so upset and restarted the game. Nothing has been as challenging for me since then.
 
That Veteran in Challenger's Cave with a team of Snorlax, Excadrill and some other OU Pokémon. Would've been easier if I wasn't underleveled.
 
Probably Red in HeartGold Version. I even traded myself two LV.100 Pokémon and still lost the first two times.

Next to that, probably Whitney's Miltank (Silver) or Lorelei (Red).
 
Red in Pokemon Gold, Silver and Crystal, and the Battle Tower in Olivine City in the Crystal version. I beat Red a few times but the Battle Tower trainers killed me. The legendary dogs (Raikou, Entei and Suicune) gave me a run for my money too, especially when they use Roar on me or run away.
 
Morty and Whitney in GSC: The only problem I had with Morty was his Gengar. DAT HYPNOSIS. In my first battle with Whitney, I lost badly. (Miltank's rollout totally slain my Quilava. >_>) But for some reason I've won the second battle easily. (Maybe because she kept missing the rollout. '-')
Steven In Ruby: It was a tough battle, especially when I was fighting against his Cradily and Armaldo.
Iris in White: I did not have ANY Pokémon that could fight against dragons. And her Haxorus is insane.
 
Candice with that arsewipe Frosslass in Snowpoint, underlevelled squad and type mismatched.
 
I'd say Wallace in R/S as a gym leader and as the champion in Emerald. Didn't he have a Kingdra that was a enormous pain?
 
Honestly never saw what the fuss about Whitney's Miltank was; I mean they gave you Machop in the exact same city. It had super-effective against the entire gym and in addition resisted Rollout.

On-topic, probably Red in the original Gold. I did a Jigglypuff solo run a while back and I had to grind it to 100 to get there (and even then I had to use half a dozen revives/full restores).
 
My hardest battle was Volkner in Platinum. My highest lv was a lv 56 Empoleon. All my others were below lv 40.
 
Iris in Black 2. She was a nightmare. This was during the rematch - she wasn't too bad for the initial match. Her first four Pokemon didn't put up a fight, but her Archeops was a killer with its Stone Edge and Acrobatics. Then, when I finally beat it, she pulled out the big gun: Haxorus. That Haxorus was the hardest Pokemon I ever faced, what with Dragon Dance and Outrage. It took me 15 Revival Herbs. Luckily my Chandelure's Flame Body was able to burn it. I kept spamming Revival Herbs until the burn caused Haxorus to faint. Thank God Iris used up her Full Restores before Haxorus. (At least this was normal mode - if it were Challenge Mode, Iris might have used a Full Restore.)

Nishino in Castelia City was also hard. His Lickilicky had four uber moves and they kept fainting my Pokemon.

Cheren was pretty hard for a first Gym Leader. Riolu had no good Fighting moves, and Cheren's Lillipup kept using Work Up.
 
My hardest battle by far was way way way back in the day when i had just gotten my first ever copy of red. I had never played pokemon. Not even knowing what to expect from the elite four, i rushex in and Agatha that old hag beat me so many times. Her gengar rocked me. Ughh, i hate you Agatha.
 
Cynthia in Black. Definitely the best, that Garchomp + Outrage and Eelektross + Dragon Claw wiped me off. First my Hax, then Excadrill, and creamed everyone else as well. Next time I took in Reshiram and Kyurem... I feel sorry now.
 
Surprisingly, I had a good time with Red. (I used the exact same team he used, but I had lower leveled pokes)

Whitney's miltank kept rolling my pokemon for 3-6 days before I finally prevailed.
 
Mine was May in Emerald, in that Cycling Road route. Our Pokemon had the same levels, but her Combusken was very hard to defeat. ): Second has to be Whitney and her Miltank, and Brawly would be the third, I guess.
 
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