| Year | Name | Special Notes | |
| 2002 | Malcolm J. Richards | Malcolm endured much ridicule early in the Tournament but proved triumphant and earned his legacy. Beware the kick in the "Malcolms"! |
|
| 2001 | Jeffrey T. Boerner | Jeff started the tournament shaky, but rallied from the second day on to capture the title convincingly. This inaugural winner of the tournament has his legacy forever tied to a running route in Northfield. The Boerner loop will live on. |
|