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Hardest battle you've had in any Pokemon game?

The toughest battle I've ever had was with Elite Four in Pokemon Black and White, surprisingly enough. It took me around 8-10 tries to get them done with and when I did the rest was easy.

Although, right now Flannery's Torkoal is going to be coming in a close second place... why can't I beat it... Oh, right, his defense.
 
It took my days to beat Brock the first time I played through yellow because I was really young and inexperienced back then and the only Pokemon I had was Pikachu. I don't think I've ever struggled with a gym leader that much before.
 
Lorelei in Yellow. If I get past her, I can beat the rest of the Elite Four, but that rarely happens. Pikachu can't take a hit and her stupid Cloyster has ridiculous Special Defense. It doesn't help that almost all of her Pokemon are part Water, meaning a Fire or Ground type still has a disadvantage.
 
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It took me at least 3 tries to get past Falkner in HeartGold, his Pidgeotto was a killer at first and wiped out my team with either it's gust or peck. However, on my third try, since my Level 9 Chikorita had some HP left, I used poison powder, which really helped and along with some of HootHoot and Ratman the Rattata's moves, I defeated Falkner.
 
I've only played the Generation 5 games, but Elesa was the most difficult for me. Her Emolgas kept pulverizing my starter and Fossil Pokemon (Which were Dewott and Archen respectively at the time) and staticizing my others which makes this overall battle very annoying. I had to use a few fresh waters and Paralyz Heals to get through this annoying battle, but I eventually did make it about three days later.
 
Tate and Liz were horrible. I would say those two are the worst, followed by Sabrina in RBY. At that point in time there were really no types that beat her and hers always seemed to outspeed everything.
 
Brock, when I made the mistake of ever choosing Charmander.
 
jeez I pwnd Red's pikachu with my piloswine. :D.

Well, my hardest battle was Wallace. his pokemon were very bulky especially tentacruel ang milotic.
 
Norman in pokemon Emerald.

Every time I got his Slaking down to critical it hit me with, a critical hit.
 
Holy crap, nearly everything in Hoenn apart from Norman, Roxanne and the actual Elite Four part of the Elite Four was hard for me in Emerald. Tate & Liza were pains in the... well, everywhere. It was nearly impossible to bet their Xatu and Claydol combo.
 
Red of HGSS course, you'll have to battle him with all his pokemon at level 80s, straight form the level 50s of Blue

imo the definition of a hard battle is how much grind and planning you need to do before taking on that trainer. In this aspect Red from HGSS definitely wins.
 
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