| Date | Time | What | Where |
| Wed. December 17 |
6 PM | Home Opener vs. Oxford | Home - IHS gym [Directions] |
| Sat. December 20 |
10 AM (bus leaves IHS at 7 AM) | Pomperaug Tournament | Away - Pomperaug Regional High School [Directions] |
| Tues. December 23 |
6 PM | New Milford | Away - New Milford [Directions] |
| Sat. December 27 |
10 AM (bus leaves IHS at 7 AM) | George Kisluk Invitational Tournament | Away - Classical Magnet (Hartford) [Directions] |
| Tues. December 30 |
10 AM | Bethel | Home - IHS gym [Directions] |
| Sat. January 3, 2009 |
10 AM - wrestlers should be at Brookfield High by 8:30 AM | Brookfield Duals (Brookfield, East Haven, Seymour) | Away - Brookfield High School [Directions] |
| Thurs. January 8 (postponed due to school cancellation) |
5 PM (bus leaves IHS at 3 PM) | New Fairfield | Away - New Fairfield High School [Directions] |
| Sat. January 10 |
9 AM (Bus leaves IHS at 6:30 AM) - note change due to impending bad weather | Bunnell Duals (Bunnell, East Haven, Guilford, Wethersfield) | Away - Bunnell [Directions] |
| Wed. January 14 |
6 PM | Weston | Away - Weston High School [Directions] |
| Sat. January 17 |
OPEN | ||
| Tues. January 20 - SENIOR NIGHT |
6 PM | Stratford | Home - Immaculate [Directions] |
| Wed. January 21 |
6 PM (approx.) - This match is to follow Barlow's scheduled match against Bunnell |
Joel Barlow | Away - Joel Barlow [Directions] |
| Sat. January 24 |
9 AM | Mustang Duals (IHS, Masuk, Thomaston, Suffield, Weston, Norwalk, Staples) | Home - Immaculate [Directions] |
| Thurs. January 29 - POSTPONED DUE TO SNOW DAY |
7 PM (Bus leaves IHS at 5 PM) | Newtown | Away - Newtown High School [Directions] |
| Sat. January 31 |
9 AM (Bus leaves IHS at 6:30 AM) | Portland Duals (Portland, Westbrook/Old Saybrook, Gilbert, Wethersfield) | Away - Portland High School [Directions] |
| Wed. February 4 |
6 PM | Pomperaug | Home - IHS gym [Directions] |
| Sat. February 7 |
9 AM | The Gilbert School | Home - IHS gym [Directions] |
| Wed. February 10 |
6 PM | Brookfield | Away - Brookfield High School [Directions] |
| Fri. & Sat. February 13 & 14 - varsity only |
Time TBA | SWC Championships | Away - New Fairfield High School [Directions] |
| Fri./Sat. February 20 & 21 - varsity only |
Friday - Registration & check in 2:30 PM, weigh-ins 3 PM 1st round matches 4:30 PM Saturday - 8 AM weigh ins, championship quarterfinals & 1st round consolations start at 9:15 AM |
Class S Championships | St. Bernard's [Directions] |
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Immaculate High School
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