After reading the title, the only thing I could think of was EVERY GAME ON STEAM.
My most fond memory of winning would probably be when I was very, very little. My parents bought a lottery ticket at a stand and let me scratch it. I won the price of a ticket, so we exchanged it for another and I won again. Repeat. Anyhow, I won 3 consecutive times and nothing on the fourth. The end result is still that I didn't win anything, but I still won the lottery 3 times mother fu**ers >_>
My most fond memory of winning would probably be when I was very, very little. My parents bought a lottery ticket at a stand and let me scratch it. I won the price of a ticket, so we exchanged it for another and I won again. Repeat. Anyhow, I won 3 consecutive times and nothing on the fourth. The end result is still that I didn't win anything, but I still won the lottery 3 times mother fu**ers >_>