Toughest Gym Leader

[EspNeon]

Claire is the toughest, no doubt.
Gyrados: Never really struggled here. Ampharos usually takes it down before it can become a problem although Intimidate does play a crucial role.
Dragonair: This is the worst ever. It's pretty much her staller. ThunderWave becomes a huge problem and DragonPulse/FireBlast finish it off relatively quickly.
Dragonair: Not as bad as the first one but still a problem. ThunderWave/Dragon Pulse can become a pain especially when it preceded Kingdra.
Kingdra: I hate this one. It's a constant problem. It's got a great defence and attack, adding Smokescreen to increase loss of accuracy and then HydroPump and HyperBeam, this easily can wipe any of my teams out.

Whitney is a close second though.
Clefairy: No problem as long as I get rid of it quickly (which I usually do). CuteCharm and double slap start to become deadly and metronome is hit or miss.I've seen worse.
Miltank: The devil. It's got a great defence and Attract followed by Stomp just becomes a road to hell. MilkDrink is just a constant pain but it's easier to defeat than Clair's Kingdra.

Chuck and Blue and Morty are fairly tough but given the right team they cause no hassle at all.

 

[bulbasean]

Whitney of course, also Chuck...

 

[Ver-mont]

Whitney and that demon she calls a Miltank.

Clair and Blue are tough too.

 

[Fugazy]

Whitney and her Miltank! My god! I hated her so much..

 

[Nurse Joy]

I hated Whitney and her Miltank and that move Milk Drink.

 

[MagnetonNr1]

Sabrina, since I had no Ghost/Dark/Bug-type moves and since I was pretty underleveled her Alakazam pretty much owned me.

 

[QueenDragonRider]

So far, in my Heartgold game, the toughest Gym Leader I faced was Chuck. Him using Focus Punch really wiped me out....

 

["Spite" DefaultAsAwesome]

Bugsy, if you're not a Cyndaquil user. Unholy **** is that Scyther tough...

 

[Howie Cheeto]

Chuck. That Poliwrath...argh.

 

[Cosmos]

Whitney wasn't that hard, although I did stack my team so it was easy. The one that irked me the most was Jasmine since I only had Maganium, Beedrill, and Victribell.

 

[BurningWhiteKyurem]

Claire had me dropping my jaws in rage when I faced her, I took care of Dragonairs and Gyarados...but then came Kingdra and 3 straight critical hit Hydro Pumps...had to rely on Espeon to finish off the match.

 

[joep05]

aside from pryce ive lost against all of them at some point... even falkner although in my defence i did have just a chikorita.

jasmine is tough because that steelix is higher in level than it should be (needless to say that pryce isnt)

i always struggled the most with whitneys miltank and mortys gengar, gottaa rule in favour of whitney

 

[ThunderPuncher]

Whitney & Claire gave me the most challenge out of all the Johto Gym Leaders.

But it seemed like Whitney was easier and Claire was harder in HGSS than they were in GSC.

 

[~Kari~]

Whitney was actually easy for me. Clair was hard because I didn't have any ice or dragon moves. Her Kingdra killed me a few times.

 

[MegaSerperior]

Whitney and Clair. Ugh those 2 are so annoying! Whitney's Miltank would get my Pokemon infatuated and then when i finally landed an attack, she just used Milk Drink. Then for Clair, all of my Pokemon except for my starter were extremely underleveled and my Meganium couldn't even touch her Pokemon.

 

[JhenMohranMH3]

Whitney's Milktank was sooooo hard because my team was rubbish at that stage :/. Clair was much much easier

 

[Sietse23]

1. Whitney
2. Claire
3. Bugsy (I didnt have Cynda)

 

[shining moons]

Whitney and Clair. They were easy since I knew their weaknesses, but they were still really flipping annoying...

 

[Zoruagible]

Clair, I got paralyzed alot

 

[dLOSINGSTREAKb]

If you dont over train, bugsy's scyther will give ou trouble. Also if you give Whitney's Miltank a change to get roll out going, that can be a huge pain