Thread: Most Difficult Gym Leader in each generation?

Gen I: I've only just started playing through Red and only got 3 badges, but the hardest so far was probably Misty
Gen II: Whitney of course.
Gen III: Tate & Liza. Never go up against them with just a Blaziken and a Linoone!
Gen IV: I don't think any of them gave me that much trouble
Gen V: Lenora. Why are the Normal type Gyms always really hard??

Gen I: Hmm... Misty for me. My pokemon team were all weak to water-types.
Gen II: None of them. They were all grand, actually.
Gen III: Winona. The reason why I caught an Altaria, too.
Gen IV: Sailed through them.
Gen V: Clay and his Excadrill. Oh dear, that was not fun. Elesa's a runner-up.

Generation I: Sabrina. And her damn Psycho Pokemon. At that time, there was NOTHING that could counter them. There were not that many good bug attacks and all the ghosts back then got owned by her, since their type was Ghost/Poison. It has been a long time ago since I played Pokemon Red, but I think I finally beat her with a Jolteon and its Pin Missile. Reason: If I remember right, Jolteon was the only Pokemon back then which could beat a Psychic type without going KO first. Or at least it was for me.
Generation II: Whitney. I hate that fricking Miltank!!! In the remakes Whitney became easier, but then I got problems with Chuck. However, Whitney still was tough. I also had some problems with Jasmine in the original games.
Generation III: I never played them. So I can say nothing here.
Generation IV: I had problems with Gardenia and Fantina.
Generation V: Elesa, I hate you! You and your damn voltswiching team!

Gen I: First time having problem against Brock with my Pikachu in Yellow. I thanks to my older sis that I must get Nidoran to defeat Brock easy.
Gen II: I cannot remembered.. =P but sure that Blair is the difficult one...

The other gens, IV and V, that i cannot remembered that too. =P but I think Eighth/Dragon Gym leader are too difficult. =P

Hmmm...
1. I say Sabrina, though I didn't have that much trouble.
2. Whitney..... D: Damn that milktank. >.<
3. Brawly I figure, mainly cause I never trained up a flying or psychic type before facing him. xD
4. No one really, Hardest for me was Fantina though.
5. Clay...My poor leavanny was crushed each time. Q.Q Other wise it's Lenora. >.<

Gen I: Seeing as I always choose the Fire Starter in every region, Misty was the hardest.
Gen II: That damn Miltank!
Gen III: For me it was Norman, that Slaking!
Gen IV: I would say Fantina because I really didnt have any Dark Pokemon or strong Dark-type moves on my team

Gen 1: Sabrina, if only because Psychic types were so overpowered.
Gen 2: Clair, though she was still easy. Mainly because you're probably underleveled, and have no Dragon moves for Kingdra. (Also, Whitney is a pushover. Seriously.)
Gen 3: Juan. Once again because of Kingdra spamming Double Team, then Chestoresting off the damage, and Double Teaming some more.
Gen 4: None, but if I had to choose, Roark. Cranidos hits hard for that point in the game.
Gen 5: Once again none, but if I have to choose, Lenora if you have no Fighting types.

Gen I: Misty. Took out my Oddish, Charmeleon, Nidoking. My Magikarp, surprisingly, took down her Starmie with a Critical Hit tackle!
Gen II:Morty...
Gen III: Wallace. Never cared about types back than...
Gen IV: Not much trouble. Crasher Wake, I guess.
Gen V: No trouble. By this point I had a good idea about types and everything.

Gen I: Brock. I wanted a charizard so bad but couldn't get past him with it... then I discovered Mankey. >:D
Gen II: Whitney. That Miltank was deadly.
Gen III: Tate & Liza. They were seriously hard to beat with the earthquake/levitate thing.

Gen I: Sabrina and that Alakazam. Also, the first time I ever played I remember royally screwing up my party and couldn't get through Erika. I lost to that Vileplume so many times.

Gen II: Clair. Dragon types, man.

Gen III: Tate and Liza.

Gen IV: Wake, probably. Most of my troubles in DP were with Cynthia.

Gen V: Yet to play it.

Gen 1: Misty. I had Charmeleon, Nidorino and Magikarp only.
Gen 2: Whitney and her bleeping Miltank.
Gen 3: Haven't fully played it yet
Gen 4: No trouble. My Infernape swept through them all, even Crasher Wake.
Gen 5: Those Voltswitching Emolgas were not fun.

Gen I: Sabrina. Psychic types are OP as crap in Gen I.
Gen II: Whitney and her stupid Miltank can go burn in hell.
Gen III: Wattson. Just Wattson.
Gen IV: Whitney is even harder the stupid dumb fsdhhfhdfj
Gen V: EDIT: LENORA I LOST SO MANY TIMES AGHHH

I: I think Sabrina almost had me in tears a few times.
II: Whitney was obviously brutal, but I think Clair caught me off guard, too.
III: After recently replaying Ruby, I can say with confidence that Tate & Liza are the worst.
VI: I really did not care about Sinnoh, so my SS choice goes back to Whitney. Clair was pwn't this time, though!
V: I've played Black, White, and Black 2, and I have yet to lose to a gym leader. This generation has three of the easiest gym leader battles I've ever experienced (Skyla, Brycen, and Marlon).

Kanto: Sabrina
Johto: Whitney
Hoenn: Tate and Liza
Sinnoh: Fantina
Unova: Drayden

Gen. I: Misty, i suppose, just because of Starmie.
Gen. II: WHITNEY. >:I
Gen. III: Tate and Liza.
Gen. IV: Fantina, she was just the longest battle for me, never really had any problems.
Gen V: Lenora, though Elesa was also really tough.