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The Gym Leader battles that surprised you the most upon your first challenge

Bugsy in HGSS. Scyther used U-Turn!

Whitney in HG. Being uneducated in Pokémon at the time, I used male Pokémon. I quickly realised the magnitude of my mistakes.
 
Sabrina's Alakazam in Fire Red. I expected it to be hard, since I lost pretty badly the first time I played the game when was younger. I defeated it in one attack with a Dugtrio. ._.

Or the first gym in Hoenn, or 2nd in Kalos. I didn't think I'd need Parlyz Heals in those types gyms. It was the most annoying thing ever. They paralyze everything, and I never get a chance to attack anything.
 
I know it's already bean said by others, but the only big surprise I've had against gym leaders was Whitney, and her Rollout using Miltank. I thought my team was reasonably leveled, but I'm not sure if I included a fighting-type. Probably that Machop that you could trade for . . . it's been a long time since that first Gold Version playthrough. Anyway, new Pokémon, new move that I had never encountered before. Wiped me out.
 
Gen 2 was my first and besides the Miltank thing. Morty's ghost pokemon sure was a surprise. I didn't know that normal didn't affect ghosts and I cried because not only could I not hit his pokemon, they were faster and I usually got OHKO'd. Also Jasmine's Steelix and hyper potion. F.M.L
 
Korrina in X/Y, because I had to battle her so many times. Also because of her Hawlucha, who can be just as dangerous as Whitney's Miltank - unless you have a Ghost-type, then it becomes laughably easy. ^^;
Ramos also surprised me, when he sent out a Weepinbell as his final Pokémon.
 
I had no idea of how dangerous a fat cow could be...

EDIT: I saw another guy commenting about Cheren and he is right. That Lillipup...
Or Skyla. Swannas Air Slash made me flinch all the time.
 
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As many around here..Whitney and miltank. :boom:
I admit too I laughed at her gym with her weak pokés (didn't prepare a fightin' type or anything) and while I was fightin' her. :spin:
It was a walk in the park until that pink cow appeared, don't remember my team but I thought I had quilava, flaafy and one more. Suddenly the battle became pretty hard with her milk drink, stomp or rollout and I quickly lost, I went to train and tried again, luckily I managed to overpower her :thumbup:, but it was haaard :dead:.
That was silver version, you bet I prepered too hard in SS to avoid such a humiliation again xD :nono:.
It was my one and only loss against a gym leader, I had kinda difficult battles but no as surprising as how bad defeated me that pink haired girl :bawl:.
 
Well this was my brother, he was challenging Korrina and that new Fighting/Flying type just OHKO'd his whole team. He was pretty surprised!
 
I have to say Whitney in SoulSilver and Lenora in White. I underestimated Whitney at first due to the gym being Normal, and all the pink and girly stuff. But once she sent out that darned Miltank, I was done for. She just kept infatuating, flinching, and OHKOing my Pokémon, that it took me several times to beat her.
I didn't expect Lenora to be much either, but once again, Normal types showed me how wrong I was. Her Watchog's Retaliate just destroyed my team completely! In order to beat her, I had to get a Fighting type, and even then it took me a few times to beat her.
I have to say Claire in SoulSilver was surprisingly tough as well, as was Valerie in Y.
 
Surprisingly, Cheren in BW2. I went in with the mindset of "First gym leader, probably a piece of cake!"...and was surprised to find that he was much more challenging than I'd expected. (Darn you, Work Up!)

Of course, ditto to Whitney as well. It's difficult to forget that cow.
 
Tate and Liza in emerald. Holy cow, they were pretty tough for me when I first fought them. Partly because of the fact that my pokemon were under-leveled.
 
Elesa in Black version. the most powerful Pokemon on my team was a Dewott, and I didn't have a ground type, plus all her electric-types were faster than most of my team. She destroyed 4 of my 5 Pokemon with Volt Switch before I brought out Boldore to tank her hits and SPAM Rock Wrecker.
*EDIT*
Norman in Ruby surprised me too, and I had to train my Swampert 10 levels higher before I challenged him again.
 
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