| DATE | CONTEST | LOCATION | TIME |
| Dec. 2, 2008 | Berean Baptist Christian School | Home | 4:30/6:00 p.m. |
| Dec. 4, 2008 | Keith School | Away | 4:30/6:00 p.m. |
| Dec. 9, 2008 | Rockford Christian (rescheduled) | Jan. 8, 2009 | |
| Dec. 12, 2008 | Ethan - Allen | Away | 6:00/7:30 p.m. |
| Dec. 15, 2008 | Alden - Hebron | Home | 5:30/7:00 p.m. |
| Dec. 18, 2008 | Faith Christian | Away | 5:45/7:30 p.m. |
| Jan. 8, 2009 | Rockford Christian (rescheduled) | Home | 4:30/6:00 p.m. |
| Jan. 9, 2009 | Christian Liberty | Home | 4:30/6:00 p.m. |
| Jan. 15, 2009 | * St. John's Military Academy (rescheduled) | Feb. 12, 2009 | |
| Jan. 20, 2009 | Berean Baptist Christian School | Away | 4:30/6:30 p.m |
| Jan. 23, 2009 | Keith School |
Home | 4:30/6:30 p.m. |
| Jan. 27, 2009 | Rockford Christian | Away | 4:30/6:00 p.m. |
| Jan. 30, 2009 | Ethan - Allen | Home | 5:30/7:00 p.m. |
| Feb. 3, 2009 | Alden- Hebron | Away | 5:30/7:00 p.m. |
| Feb. 6, 2009 | Faith Christian | Home | 5:30/7:00 p.m. |
| Feb. 10 , 2009 | Christian Liberty | Away | 4:30/6:00 p.m. |
| Feb. 12, 2009 | * St. John's Military Academy | Home | 4:30/6:00 p.m. |
| Feb. 13, 2009 | Maranatha | Home | 5:30/7:00 p.m. |
| Feb. 17, 2009 | * Kenosha Christian Life | Home | 5:30/7:00 p.m. |
| Feb. 20, 2009 | * Calvary Baptist - Men. Falls | Away | 6:00/7:30 p.m. |
| Feb. 24, 2009 | * Union Grove Christian | Home | 5:00/6:30 p.m. |
| Feb. 26, 2009 | Maranatha | Away | 4:30/6:00 p.m. |
| March 3, 2009 | WIAA Boys Regional | TBA | 7:00 p.m. |
* Non Conference