The entire joke of this series is that Player can never win a single game. However, there are times when the factors behind his defeat are too unrealistic, and they happen so often that it deserves its own page:
- Episode 2: After Player (as Impostor) manages to convince Mother to vote Bro, Mr. Cheese (his co-impostor who was ejected earlier in the game) shows up out of nowhere and asks Player if he has won as impostor yet.
- Episode 10: Even though Player failed to kill The Gentlebot, he should have won the game anyways because Veteran successfully killed Mr. Cheese, meaning that the number of crewmates (Gentlebot and Captain) was the same as the number of impostors.
- Episode 13: Player wins his first game by cheating and is sent to the cheaters lobby... except that Blue and Not-Orange (the main cheaters) are not sent to the lobby.
- Episode 14: Mr. Cheese being sent to the Cheaters Lobby for his actions in Episode 10 makes sense, but he had appeared in Episodes 11 and 12. By contrast, Player respawns in the lobby immediately after his first victory.
- Episode 16: Veteran kills The Gentleman within 10 seconds of Noob getting ejected.
- The King Impostor: After a hot streak, Player thinks he can win the game by killing Hornsly, but it turns out to be a decoy set up by his pet robot QWERTY. QWERTY proceeds to eject Navigation from The Skeld, then blows it up.
- Airship Arrival: A similar situation to what happened in episode 2 — Player convinces Veteran that Poopyfarts is the impostor... then it is revealed that the latter recorded Player saying that he just needed one more kill to win the game.
- Player lampshades it in Fat Impostor, going into a huge rant about how often his victory is snatched away from him by something completely random to Veteran and how he's cottoned on that Veteran has something he's going to reveal at the last minute to screw him over. When Player concludes by screaming that he's ready for whatever Ass Pull Veteran has planned, Veteran just shoots him in the face.
- The Cold Open of this episode not only has a set of close-able doors in a place where there shouldn't be any, but is also revealed to be a mod, which Player was unaware of the whole game.
