It depends entirely how you define a particular game. My poker example is in reference to winning a single hand. In that case, one hand is a single game. This makes poker highly variable and effectively impossible to win every time despite perfect play. In real life poker, this is mitigated by playing many hands over a long period of time.

In the case of single-player games such as FTL, people really do mean one single game when they talk about winning or losing. Otherwise, your odds of winning no matter how bad you are begin to approach 100% if you play enough games.