Hardest battle you've had in any Pokemon game?

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.
 
Wallace in Emerald. I hated going against that Milotic. Red in HG/SS comes close.
 
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.
 
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!
 
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.
 
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.
 
I agree about may under the cycling road, the starter in that battle was always vicious.
 
X-Lan said:
I agree about may under the cycling road, the starter in that battle was always vicious.
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That Grovyle was such a pain, put the smack down on my Marshtomp, I didn't have a Taillow on my team... x/
Combusken on my other runs through was trouble as well, Marshtomp however crumbles with any grass type move.
 
The 2 twins in emerald who run that gym Claydol and Solrock or w/e it was is a pain....
 
Evice in Pokemon Colosseum. I was way too many levels behind him the first time and was only able to get through with dumb luck.
 
Tate and Liza of Hoenn was so hard. I was a begnning trainer at that point and had Blaziken and others between levels 20-25. I actually won because my Wobbufet used Destiny bond.
 
Tate and Liza, it took me 3 days to beat them.
But they're not just beyond annoying, they're far beyond annoying.
In emerald that is. They were pretty easy in RS.
 
cynthia from pearl. she was a beast and the only properly leveled pokemon in my party was my torterra and palkia :P
 
I think the hardest battles for me were both in the Hoenn Region:
The Double Battle fight Tate and Liza was pretty hard, especially since i had Blaziken.
But the hardest battle ever for me was Champion Steven and his Metagross...
 
I had difficulty with the champion of R/S/E. I'm talking about both champions, Steven in Ruby/Sapphire and Wallace in Emerald. My Pokémon weren't that very strong at that time. Steven's Metagross was hard to beat for sure, and I had trouble with Wallace because his Water-type Pokémon had Ice-type moves, and it would greatly damage Sceptile, my starter.

Other than that, Tate and Liza was also a hard duo to beat, especially in Emerald since they had additional two Pokémon. I hate it when they use a Hyper Potion, and they have two of it!
 
Tate and Liza take the cake.
However in hacked games, Wood's Leafeon (Victory Fire version)
Has nuts defense, holds a sitrus berry, is only second gym, leader has 5 super potions.
I hated him so much.
 
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