2nd Gen Those 'Throw your GBC at the TV' moments.

[Raichu1988]

Blue version: When my game save stopped saving and I was only 2 pokemon away from completing the pokedex. >.> I was pretty sure I was going to break my gameboy color, but I didn't since it was all I had.

Silver version: Did the same thing, died again but I only had 200 something so *shrug* I did however, have many hours of game play and breeding on it. That ticked me off like no other.

Yellow Version: When my sister played a new file and ruined my level 99 Pikachu.. *!%#!! I had never been so mad since I spent so much time raising it and playing. I gave up on that point, sold my yellow version and didn't play until another yellow version a few years later.

 

[TrinityLimit]

Whitneys miltank always pissed me off for some reason..

 

[Yukima]

Crystal was my first Pokemon game, and I had quite a few stupid things happen to me...

Like those times I fought Whitney's Miltank and kept on losing and whiting out, and didn't realize that by saving BEFORE fighting her, I wouldn't have to keep losing lots and lots of money.

And when I watered Sudowoodo and accidentally pressed "Run" instead of "Fight" and forgot to save beforehand!

And when I accidentally knocked out Suicune and saved afterward...

And... when I was about to catch Lugia and couldn't because I forgot to switch my Box!!

 

[Dirtyjerry]

1. Searching for the legendary dogs.
2. Playing forever to train my Typhlosion to level 100 (which was a big achievement back then) only to find the power shut off minutes later.
3.Catching Mewtwo.
4.Pokeballs not working in general.