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What was the hardest Gym Battle you've ever fought???

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Okay so I'm sure this questions been asked before but...


Mine was when i was battling Whitney in Gold.

I easily won against her Clefairy but...

when I got to Miltank it kept just using Rollout without missing and Milk Drink and Attract just got annoying after a while.

I swear that was probably the first time I wanted to throw my Game Boy against the wall.

So what was yours??
 
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Two actually:

The first time I played Silver, Whitney frustrated me to no end. In recent years though, I've managed to find a way around her

The one that's constantly frustrating me though is Brawly. In RSE, I never seem to be strong enough to face him when I get to his gym. I had a moderately easy time in my most recent Emerald playthrough with my Combusken, but I swear that guy's harder than he should be for me (I don't like training a random bird I'll probably never use again just to fight him so that makes things more difficult)
 
I would definently have to say either Whitney in Gold, or Fatina in Diamond. I could never get either that dang Miltank or that stupid Mismagius.
 
Yeah, Whitney was hard for me the first time I played. With you there.

Other than that, NORMAN KEPT OWNING ME IN EMERALD. And Sapphire. He tends to kick my ass, because my team is just not ready for his line-up at that time of the game. D: Slakings...
 
I don't remember any of the earlier ones, but the most recent was Crasher Wake in Platinum. This is the first game where I went out of my way to use only pokemon I felt like using, type advantages be damned, and my best chance was my severely underleveled raichu (which was always fainting anyway). Thinking back to it I have no idea why it was so hard for me, but I will forever hold a grudge against Crasher Wake and his stupid water puzzle things no matter how awesome his theme song is.
 
I can remember my battle with Winona in Emerald being seriously difficult- I won over each one of her Pokemon but that Altaria really bashed me... seeing how all my Pokemon were in 30s with only my starter(Grovyle) at lvl 35, and no means whatsoever to tackle Dragons, it was really difficult. (I obviously didn't know about the ICE BEAM TM in the Abandoned ship-I laughed at myself as I saw my Pelliper OHKOing the Altaria)
 
Let's see...

Norman (Sapphire) - Why, oh why did he have 2 Slaking? Those things were hard to beat!

Winona (Sapphire) - I had nothing to do against her Altaria, so I was forced to spam Swampert's Surf. On a side-note, Swampert was the only Pokemon I trained at that time.

Wallace (Sapphire) - Darn Milotic

Tate and Liza (Emerald) - I remember seeing their Xatu use Sunny Day and their Claydol, Lunatone and Solrock surviving with around 10-20% of their HP remaining when I used Surf.
 
Certainly Whitney, which is why I am saddened that they have made her Miltank lower leveled in HG/SS. The newer games are so easy :[
 
Bugsy in Silver and Winona in Sapphire. THat's what you get for training grass types.
 
Battling against Misty back in Red. Mainly because my starter Pokémon was Charmander.
 
Norman in Ruby for some reason. I didn't have any fighting pokemon, and the pokemon I did have with fighting moves were all pretty weak. I took me multiple trys to beat him.
 
Tate&Liza in Emerald. I really loathe those twins. Solrock kept using Solarbeam on my Swampert in sunny weather made by Xatu and Claydol used Earthquake over and over and over.

Whitney in Silver. That Miltank.
 
Clair, and only because of Kingdra too. I didn't even know what a Dragon Type was when I fought her, so I was trying to figure out why my ampharos couldn't hurt Kingdra lol
 
Misty's stupid starmie kept beating my charmander and even when i got a pikachu to help i still couldn't win! I just ended up getting them to ridiculously high levels and even the i just barely won-_-
 
Yeah I had that problem in FRLG, but on my most recent playthrough, all I had was a Nidran m and a Wartortle and I beat her pretty soundly.
 
Fantina.
Until:
27th (or was it 26th?) Try
LUXRAY used Crunch!
It's super effective!
MISMAGIUS fainted!
 
Almost every one in Sapphire.
Even if all my pokemons had like 10 levels more than the opponents pokemons, I still had hard time and lost several times.
 
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