I think it was a very interesting choice to have Dean and Crowley play foosball against two men who appear to be twins. If they’re not twins, they’re certainly brothers at the very least. One of them is wearing a red plaid similar to a shirt Sam had on early in the episode, and the other is wearing a more muted, neutral color, similar to something Dean would be more likely to wear. They make a great team, and end up winning as a result of Crowley’s inability to stop talking when they should be focusing on playing the game.
Crowley seemed confident in his wager, but his lack of focus on what is truly important, what is right in front of him, is the reason he can’t win the game of foosball, and won’t win the game he’s playing with Dean.