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Trying to fight Claire in SS with only Pokemon based on predatory animals. Also they're underleveled.
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Definitely Whitney. Her Miltank has godlike strength.
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I found the battle with Cynthia in Black to be very difficult.
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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. |
Either Glacia in Emerald or Aaron from D/P/Pt
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Candice with that arsewipe Frosslass in Snowpoint, underlevelled squad and type mismatched.
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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?
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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.
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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.
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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.
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For me the hardest battle I've ever had is Shauntal in BW1, she managed to DESTROY my Arceus in lvl 89, even with type disadvantage.
Second, I think is Elesa in BW2, I hate that Emolga. Besides that, Cynthia in BW2 is a *****. |
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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Red on the Gen II remakes was pretty darn hard. I had to trade over some of my better Pokemon from Diamond version to battle him. Took me two tries and a crazy amount of Pokemon reviving and health restoring.
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Wallace in Emerald. I hated going against that Milotic. Red in HG/SS comes close.
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Honestly, Sidney from the Hoenn Elite Four. I HATED him so much. That Shiftry... and Cacturne, not to mention I always picked Swampert. I got beaten by that guy so many times.
The rest of the Elite Four in Hoenn? Champion? Pushovers. But Sidney... *shudder* Second has to be May when she's in front of the Lilycove Department store. I wanted to get in there so badly, but no matter what I did, my Pokemon always seemed drastically underlevelled for that battle. Took me so long to beat. |
Rival as the champ in Red. I had an oddish left and he had a venasaur left and it took me an hour to beat him by using cut.
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Oh god I suddenly started having Flashbacks to Cynthia in Diamond version. I repeat, oh god.
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The hardest battle that I eventually won was Ghetsis in Black. It took me three attempts to do so, and it ended up in a 1-on-1 battle between us. It's also one of the few battles that I've physically felt exhausted after finishing it, which never normally happens with me in Pokemon games. Granted, I was probably a fair bit underlevelled (which also never usually happens) but still... it was hard, guys!
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My opinion on this has changed over the years, and currently I have to say Sabrina from yellow or Whitney from gold and silver if I start with Chikorita.
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Pokemon Champion Gary/Blue in Pokemon Yellow, I can barely remember the fight as I was much younger, however that Arcanine proved to be a handful.
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I agree about may under the cycling road, the starter in that battle was always vicious.
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I remember battling my rival in firered when he was champion. On like my 15th try I beat him on a lucky critical hit after my Blastoise luckily held on at 3 HP.
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