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What battle almost made you rage quit? Or holds special meaning?

The battle with Blue the second time around in FR/LG was always a massive hassle for me. His Pokemon were increased a good 10 levels I believe and I never knew what to do with his Tyranitar. Other than that the only other one that rings a bell is the battle with Liza & Tate in Emerald, especially when you chose Torchic as your starter.
 
This is the first Gen I've started comp. online battling and I have only used one team so far with succes. My team is a mix of OU and UU which consits out of Froslass, Scyther, Slowbro, Gengar, Milotic and Weavile. So I face this (probably) moron kid. He had like a loisy Battle Maison Streak, only 13 evolutions but he brought all his ingame legendaries with Poké-Bank. His team was Zekrom, Mewtwo, Deoxys-S, Tyrantrum, Yveltal and Rayquaza. I thought, why not? So it comes down to me winning 2-0 and just before I'm about to crush his last uber with my boss Slowbro, the communication breaks which means I couldn't save the video. I really hope the dude's game crashes and he loses his damn ubers.. Sorry for the rage, but cm'on, I've had Slowbro make fun out of a team of Ubers (a)
 
Probably the most frustrating battle for me has to be Tate & Liza. Their double battle was especially hard and painful, plus they had 2 instead of just one hyper potion...having picked Blaziken as a starter didnt make things easier. The most special battle for me to this day has to be the final rival battle in both the 1st gen games and FR/LG remakes. As a kid, thinking you had beat the game by barely defeating Lance, just to find out your rival had beaten you too it made my heart go wild. When i replay FR/LG, its still one of my favorite moments of playing Pokemon.
 
When I first played Silver, I wasn't even courageous enough to fight Red. When he sent out a level 81 Pikachu and I had my level 50-something Typhlosion on my party, I immediately turned my game boy off. Needless to say, first time I actually attempted to fight against him with some Pokemon around level 60 (did some grinding), I got stomped so many times I lost count.

Jamais said:
Never in the first 10 years that I'd played Pokemon had I had any struggles against any of the Gym Leaders... until I came across Roxie in White 2. The only 2 Pokemon I had at the time were a Snivy and Riolu- neither of which stood much of a chance against Roxie, even though they were ~5 levels higher than her Pokemon. I was too stubborn to go and catch another Pokemon or grind them for a few more levels in order to take her out, which led to me losing to her 5 times in a row. I honestly stopped playing for a day or two, grabbed a Druddigon from the Dream World, and continued as if nothing had ever happened.
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A level 12 Magnemite with couple of potions would've easily owned that gym unless you were playing challenge mode. I'm quite surprised you didn't struggle at all against the likes of Whitney, Norman, and Tate/Liza only to be stomped by Roxie.
 
Aeroblast said:
A level 12 Magnemite with couple of potions would've easily owned that gym unless you were playing challenge mode. I'm quite surprised you didn't struggle at all against the likes of Whitney, Norman, and Tate/Liza only to be stomped by Roxie.
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Like I said, I was too stubborn to go and catch a Magnemite, since I really don't like them (and I didn't want to catch a Pokemon for just one battle and never use it again). The other battles are pretty easy with a bit of strategy, but so early into the game, I didn't give myself much to work with.
 
My third battle with Red in Pokemon HeartGold. It was my third attempt at the battle, and the first time I won.
 
Jamais said:
Like I said, I was too stubborn to go and catch a Magnemite, since I really don't like them (and I didn't want to catch a Pokemon for just one battle and never use it again). The other battles are pretty easy with a bit of strategy, but so early into the game, I didn't give myself much to work with.
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So basically you handicapped yourself unwittingly.

Kind of gives me a faint idea for a challenge, actually.
 
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