| Player | Team(s) | Consecutive Wins |
| Marc Horner | Underground Jimmy, Underground Tim | 5 |
| Jason Brehmer | Underground Jason | 4 |
| Jon Ray | Underground Art, Underground Hank | 4 |
| Justin Gunderson | Underground Jeff, Underground Jimmy | 3 |
| Brian Leisure | Underground Art, Underground Austin, Underground Dan, Underground Jeff | 3 |