| Date | Game | Time |
| December 4, 2008 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| December 11 2008 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| December 18 2008 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| December 26, 2008 | Proviso West Holiday Tournament Session 1 Saint Joseph vs. Homewood Flossmoor Whitney Young vs. Proviso East Glenbrook North vs. Hillcrest Morton vs. Von Steuben Session 2 Forman vs. Fenwick Proviso West vs. New Trier Zion-Benton vs. T.F. North Evanston vs. Saint Patrick |
9:00 AM 10:30 AM 12:15 PM 1:45 PM 3:45 PM 5:15 PM 7:00 PM 8:30 PM |
| December 27, 2008 | Proviso West Holiday Tournament Session 1 Proviso East vs. St. Joseph Hillcrest vs. Von Steuben Forman vs. New Trier T.F. North vs. Evanston Session 2 Whitney Young vs. Homewood Flossmoor Morton vs. Glenbrook North Proviso West vs. Fenwick Zion-Benton vs. Saint Patrick |
9:00 AM 10:30 AM 12:15 PM 1:45 PM 3:45 PM 5:15 PM 7:00 PM 8:30 PM |
| December 29, 2008 | Proviso West Holiday Tournament Session 1 Session 2 Teams to be determined |
11:00 AM 6:30 PM |
| December 30, 2008 | Proviso West Holiday Tournament Session 1 Session 2 Teams to be determined |
11:00 AM 6:30 PM |
| January 8, 2009 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| January 15, 2009 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| January 22, 2009 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| January 29, 2009 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| February 5, 2009 | Prep Sports Insight; Interactive Sports Web Show | 7:30 PM CST |
| February 7, 2009 | Basketball - St. Xavier College @ Robert Morris College - Women's Game | 5:30 PM CST |
| February 7, 2009 | Basketball - St. Xavier College @ Robert Morris College - Men's Game | 7:30 PM CST |