| Sedgwick Bowl | Year | Owner | Team |
|---|---|---|---|
| Sedgwick Bowl I | 1994 | Matt Vitiello | Vitiello Pimps |
| Sedgwick Bowl II | 1995 | Nando DiFino | Isle Of Ewe |
| Sedgwick Bowl III | 1996 | John Tooley | Wide Right |
| Sedgwick Bowl IV | 1997 | Marc Cusano | Sonny Red |
| Sedgwick Bowl V | 1998 | Jeff Ascenzo | Corleone Jews |
| Sedgwick Bowl VI | 1999 | Matt Cusano | Polish Falcons |
| Sedgwick Bowl VII | 2000 | Mike Cusano | Klein Hall Crackas |
| Team | Wins | Losses | Division Record | Win Pctg. | Games Back |
|---|---|---|---|---|---|
| *Those Damn Dudleys (Brook) | 8 | 5 | 3 - 1 | .615 | - |
| #Sloppy Grints (Kirsch) | 6 | 7 | 1 - 3 | .462 | 2 |
| #The Wobbly H's (Mike I.) | 3 | 10 | 2 - 2 | .231 | 5 |
| Team | Wins | Losses | Division Record | Win Pctg. | Games Back |
|---|---|---|---|---|---|
| *Wide Right (John) | 11 | 2 | 4 - 0 | .846 | - |
| #Know Your Damn Role (Jeff) | 10 | 3 | 2 - 2 | .769 | 1 |
| #The Phu de kikes (Steve) | 5 | 8 | 0 - 4 | .385 | 6 |
| Team | Wins | Losses | Division Record | Win Pctg. | Games Back |
|---|---|---|---|---|---|
| *Klein Hall Crackas (Chief) | 8 | 5 | 3 - 1 | .615 | - |
| #Polish Falcons (Matt) | 8 | 5 | 3 - 1 | .615 | - |
| #Sonny Red (Marc) | 2 | 11 | 0 - 4 | .154 | 6 |
| Team | Wins | Losses | Division Record | Win Pctg. | Games Back |
|---|---|---|---|---|---|
| *The Lonely Punters (Anthony) | 7 | 6 | 3 - 1 | .538 | - |
| #Big Fat Prostitutes (Dave) | 7 | 6 | 3 - 1 | .538 | - |
| #EL Fudge (Nando) | 3 | 10 | 0 - 4 | .231 | 4 |
| Conference Championships | Sedgwick Bowl 7 | Sedgwick Bowl 7 Champion |
|---|---|---|
| Those Damn Dudleys (8-5) | ||
| Wide Right (11-2) | Those Damn Dudleys (9-5) 120-85 | |
| Klein Hall Crackas (10-5) 124-115 | ||
| Klein Hall Crackas (8-5) | Klein Hall Crackas (9-5) 117-108 | |
| The Lonely Punters (7-6) |