Most Difficult Gym Leader in each generation?

[GatoRage]

Gen I: Sabrina. Misty was challenging the first time I played because I picked Squirtle and had to rely on my Paras using Bullet Seed.
Gen II: Whitney's Miltank. It kept infatuating my pokemon -_-
Gen III: Tate and Lisa. Norman was hard when I picked Mudkip as my starter.
Gen IV: None of hem were that hard for me, but Fantina in Platnium gave me trouble.
Gen V: Elesa and her god damn Volt Switch Emonga.

I think Bullet Seed was introduced in Gen 3.

 

[Charbok]

^ I meant in FR/LG. I never actually played the original Red and Blue so I guess that one doesn't count.

 

[aristides]

I always managed to beat each gym easy on my first or second try. I had most trouble with Norman.Beat him on my first try. I lost all my pokemon except a low leveled lileep to slackoth and vigoroth. Slacking was tough for a level 8 lileep but I got through. Kept using focus punch while I made him lose focus. Plus he slacks off a lot.

 

[Articwolf10]

Gen I: OH MY GOD!!! Brock in Yellow.Me being about 7 years old aat the tie and not knowing Fighting was SE against him...

Gen II: Whitney we shoukd judt declair her the hardest gym leader ever shall we... I mean she has to have aa million votes...

Gen III: God Tate and Lisa in Emerald plus damn Wallace (I had a way underleveled team the last time I playedit) And the person who recommended a flying type against them is nuts Solrock and Lunatone are SE against them Xatu resists Flying and Claydol knows Ancient PowerI think)

Gen IV: Was pretty easy really but I was a lot older

Gen V Way to easy in White myteam was way overlevled and in white... still working up my team but I'mm going to stall the hell out of Lenora with my Litwick

 

[Karpi]

1st Gen: I know it's not a real gym, but the Fighting Dojo was more challenging than any of the regular gyms. Those stupid Primeapes with their high attack and speed were almost the end of me, plus the fact that you can get into the Dojo when your pokemon are still to weak to beat it, yet I have an obsession with not giving up till I win.

2nd Gen: Chuck was the toughest for sure. My team didn't have any defense against fighting moves and I almost lost to his gym trainers. Primeapes and Machokes again... I need a psychic type...

3rd Gen: Wattson is absolutely evil if you don't have Marshtomp. I vote him hands down. Magneton that early in the game is just not fair!

4th Gen: None of the gyms were especially dangerous, I would rate Team Plasma's admins much higher in difficulty.

5th Gen: Honestly, they were all easy. I was slightly afraid of Skyla, but I ended up winning. I guess I did lose to Iris the first time - like, a legitimate loss. Since she's one of my only losses, she probably wins overall.

 

[Noctis]

Gen I: Misty because of her Starmie in Red and Blue and Koga because of his Venomoth in Yellow.
Gen II: Whitney because of her Miltank.
Gen III: The Hoenn Gyms aren't hard to beat, in my opinion. However, Wattson is quite difficult to defeat because of his Magneton.
Gen IV: The Diamond and Pearl Sinnoh Gyms are easy to beat, but the Platinum Gyms are harder to beat. Especially Fantina with her Mismagius.
Gen V: Lenora. Her Herdier and Watchog are pretty strong for so early in the game. Furthermore, Watchog's Retalliate is a dangerous move.

 

[Isaac Gravity]

Gen I (original)- Due to the level scaling of the game. The Gym Leaders put up a good fight but the only Gym Leader to ever make me struggle a bit was Koga. Otherwise, that dude with the Level 20 Butterfree on Route 6 served more a challenge than most Gym/Elite Battles.

Gen II- Whitney. You just didn't see that Miltank coming. At that point everything is painfully easy, you may even get cocky and just focus on letting your starter do all the work. Them BAM. Miltank. After being forced to balance party levels and now have high hopes for the game, it's all back to being painfully easy.

Gen III- Norman naturally. Even if you attempt to type match-ish against them Liza and Tate will give you good fight no matter what. And since I don't try to have every element on me and play solely with those I like (at that point: Torchic, Aron and an Electrike), fighting Flannery was very dragged out. Got more annoying in Emerald as her AI got smarter. EDIT: A nod goes to Wattson and that painful Magneton as well.

Gen IV- Eh. I found fighting the Galactic Admins more of a struggle. But because of how I chose to play (forsaking the Starters who I didn't like and went and made a Shinx [which evolved to Luxio] my main), I have to give it to Roark. Sure, I chose to bring a knife to a gun fight but he sure didn't hold back any.

Gen V- Burgh. Because of my two-man party setup at that point, he wrecked me. The most thrilling fight for me since I really had a to work an actual strategy to win. Also made me possess great respect for Leavanny.

 

[ZMT123]

Gen 1-Lt. Surge
Gen 2-Clair
Gen 3-Norman
Gen 4-Maylene
Gen 5-Burgh

 

[Loliqueen]

Gen 1- For me, Koga. I have no idea why.
Gen 2- Bugsy because I had a Bayleef. ;-;
Gen 3- Flannery
Gen 4- They were all pretty easy for me actually, lolol
Gen 5- Elesa >_<

 

[New Game Plus]

Gen I: Brock (For Yellow Version)
Gen II: Whitney (Because of her notorious Miltank)
Gen III: Flannery (Because of her Torkoal)
Gen IV: Fantina (In Platinum because of her Mismagus)
Gen V: Elesa (Because of her freaking Emolga.)

 

[Soft Drink]

In RBY and FRLG it was a tie between Misty and Sabrina. Starmie was way too overpowered and Sabrina's Alakazam was a nightmare to get past with my Venasaur.
In GSC and HGSS I can't deny that Whitney's Miltank pissed me off more than once, especially with milk drink.
In the third Gen I seemed to skate by the leaders pretty easily, but the only one that was a close call was the twins.
Platinum ruined my streak with Fantina. She completely outclassed my entire team with her Mismagius.
On my only playthrough of White I didn't have a problem with anyone. The hardest trainer for me was Ghetsis.

 

[βƹβƹ ɱɪɢηѻη]

Generation I: Sabrina.. Next is Koga I believe..
Generation II: Without a doubt, Whitney. MILTANK.... mooooooOOOOOOOO
Generation III: Norman, jeez.. What's with Game Freak making normal-typed gym leaders so difficult?? :/
Generation IV: First time around, it was Gardenia. The rest of the time, Byron. This is due to the lack of fire-types. Not really, since I'm not really interested in them.
Generation V: Aloe was a toughie the first play-through. Iris is pretty hard, since I didn't want to use any of the Ice and Dragon-typed Pokemon.

 

[AshK]

1st Gen: I always had troubles with Misty. Starmie's bubblebeam was brutal. Even if I used pikachu, its defensively vulnerable.

2nd Gen: I alway have problem with Bugsie's scyther. Completely unstoppable if its faster then my entire team and has used fury cutter for like 4 or 5 straight times.

3rd Gen: Unless you have a fire, ground or fighting type Wattson is really tough because of its friggen magnemite and magnaton. Norman was also really tough since I always go at him under leveled.

4th Gen: Crasher Wake in Platinum is the toughest for me. Gyrados in general and his floatzel and his damn ice fang!!

5th Gen: Elesa for sure. All of her pokemon knows that annoying volt switch move (even her zebra pokemon which people overlook on here) Emolga is tough because of its flying characteristic actually,and my team was not ready for that yet.Although I had to train an electric type for the flying gym or else that would have been the hardest.

 

[Space Opera]

Gen I: Koga. Whenever I got to Fuchsia City, I never had anything super-effective against his Pokémon, and I was usually under-leveled.

Gen II: Chuck. Pretty much the same story as above.

Gen III: Norman, because I'm usually under-leveled, and my team's usually pathetic.

Gen IV: Crasher Wake. I always forget about his Floatzel's Ice Fang and send in my Torterra...

Gen V: Lenora's Watchog's Retaliate always gets me, and her Herdier usually manages to take down my first Pokémon. I know there are Fighting-type Pokémon nearby, but I never catch any.

 

[Juzey]

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??

 

[Likeitornot.]

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.

 

[DarkMoonsDream]

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!

 

[JoyJoyfulRabbit]

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

 

[Dolce]

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. >.<

 

[shinycharizard1993]

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