In the first season, Will Wheaton only won 4 out of 16 games. Two of those were team wins against the game, and one was a three-way tie. His only solo victory was in Star Fluxx.
The filming schedule was as follows: Wil shoots the introductions for the two episodes they are filming that day. Then the players for the first game arrive, go to makeup and wardrobe, then spend about an hour with the game publisher's rep and Ivan Van Norman, the show's games expert, to make sure the players understand the game and its basic strategy. While they do that, Wil shoots the rules explanation for each game. The game is then played in two parts. After the first part, the players are interviewed about what they did in the first half of the game. Next, the second half of the game is played, until there is a winner. They shoot the loser's couch segment and the trophy segment. Lastly, the players are interviewed about what they did in the second half of the game. Wil and the crew break for lunch, while the players for game 2 show up and start the process all over again.
In the first three seasons Felicia Day won 3 out of 9 games she played.
In the third episode of the first season, Ryan Higa wins all three of the games he, Wil, Freddie Wong, and Rod Roddenberry were playing: Tsuro, Zombie Dice, and Get Bit!