OH MY GOD WHITNEY
Brock in R/B (your first gym battle)
Brock in yellow (immune to your starter)
Red in 2nd gen
Red in 4th gen
Steven Stone Champion Battle
Gary Oak Champion Battle
May beside the cycling road (maybe I was just underleveled there)
First Battle Against Gary Oak (first ever battle)
Lance Champion Battle
Cynthia Champion Battle
Tate & Liza Mossdeep Gym Battle
other, please specify
Definately Red in gen 4. Got hammered the 1st time went in. His pokemon levels took me by surprise.... Big Time.... Took ages to train up to beat him.
HG FC: 5027 9550 8649
White FC: 0733 3989 5528
I haven't played Gen 4 yet so i'm gonna say Red in Gen 2. If I rememeber correctly that was one of the few battles that I lost the first time.
DEFINITELY WHITNEY in Gen. 2. Two words: Miltank, Rollout.
Red in SoulSilver, so fugging much. Took me like 20 tries to beat him.
I also had a hard time with Bruno in Blue, probably because my team looked something like this:
Pikachu lv. 86
Venusaur lv. 45
Graveler lv. 33
Ninetales lv. 32
Poliwhirl lv. 27
Pidgey lv. 17
Also Whitney, but only in second gen. I beat her on my first or second try in SoulSilver.
And Norman, and Tate & Liza.
Anything in the Battle Facilities, since your team is forced to be the same level as your opponents' and you can't use items. My current plan for getting through the Battle Tower is to level up a Wobbuffet, Lucario, and something else (Gyarados?) and über my way through.
For a more specific answer, Cal in HGSS is always a problem, for the same reasons as the Battle Frontier and because, if my Ampharos' Thunder misses his Feraligatr on the first shot, I am guaranteed to lose.
I fear naught but save file corruption.
Pearl FC: 0303 6397 4251
HeartGold FC: 0260 6900 8265
Black FC: 0819 3491 8420
Battling Candice in Pearl was probably my hardest battle ever, since I was only training Torterra. x_x
If only I had the Squirtbottle
I'd be able to reach Enju City
But no matter how many times
No matter how many times
I can't defeat Akane!
And then there's Wattson and his Manectric with a Shock Wave that would OHKO my team. Given Manectric was faster than everything except Ninjask...
On the other hand, I get the feeling Norman would've been impossible-hard... if I didn't have a Shedinja. By the time I send it, he didn't have anything to counter it.
I voted other, becuase I agree that Cyrus in distortion world was one of the hardest. Lance (champion) was hard in HG though, since our last pokes were my Red Gyarados against his dragonite (of course the one with thunder). I found Lance+Clair easy, even with an underleveled team. Silver w/Feralgatr helped a lot.
My Black Team
i'd go for Red, he sent my 70's team packing, but i'll face him again This Friday...
But May in the Cycling Road was pretty hard too, i thought i was the only one ^__^
Tate and Liza when all you have is a Blaziken..............
The first time I went against Cyrus at Distortion World, he beated the crap out of me.
Then... Cynthia, I had to rebattle her like three or four times to beat her.
That was pretty hard for me :(
"I'm your new God. A better one. So you will bow down, profess your love unto Me, Your Lord. Or I shall destroy you."
Red in Gen 4. Level 80s. Do I need to specify? (My team was in the 60s.)
99 % of the food you eat has previously been crapped on by aliens.
Tate and Liza battle! It was so hard! I hate Solarbeam now. :|