| Year | Male Winner | Female Winner | ||
| 1999 | Nick Stanko: Wyandotte Roosevelt | Nicole Martin: Woodhaven | ||
| 2000 | Chis DeSana: Southgate Anderson | Krissy Balamucki: Wyandotte Roosevelt | ||
| 2001 | Robert Kononowech: Cabrini | Tara Kennedy: Woodhaven | ||
| 2002 | Scott Kallgren: Trenton | Katy Jackson: Grosse Ile | ||
| 2003 | Harley Rohloff: Grosse Ile | Jaclyn Gaydos: Allen Park | ||
| 2004 | Christopher McCabe: Cabrini | Lauren Dennisuk: Trenton | ||
| 2005 | Michael Smoot: Trenton | Three Winners: | ||
| Joye Kallgren: Trenton | ||||
| Tricia Kowalski: Riverview | ||||
| Jazmin Williams: Gibraltar Carlson | ||||
| 2006 | Kyle Terpak: Riverview | Claire Stavenga: Gibraltar Carlson | ||
| 2007 | Jacob Radcliffe: Grosse Ile | Kelly McGauley: Trenton | ||