Worst game you've won?

The Binding of Isaac.
Was one of the first games I won on this site and my first rogue-like ever. It's the source of my deep aversion for the roguelike genre in general. Words can't express how much I hated that game. To make up for it I got another copy and gifted it back to the community.

Make it indie...

Day One : Garry's Incident

I don't think I've won a genuinely bad game. Then again, I'm fairly selective. If I had to pick one I think I'd go with Ballpoint Universe. The art was amazing but the game itself was kinda meh.

lol I entered a game just for the lolz then I was really mad when i got it. This game is "Dwarfs!?" (shittiest game on earth)

Voxelized. Has to be one the most bare-bones game I've ever played in my life. Two minutes into the game, and I'd seen all the content.

Deadly Profits