| Match Date | Team | Immaculate | Opponent |
| Wed. December 17 | Oxford | 69 | 12 |
| Sat. December 20 | Pomperaug Tournament | Immaculate finishes 6th | Congratulations to 1st place finisher Gavin Buckley at 130, 2nd placers Andrew Cronin at 135 and Connor Policastro at 171, 3rd placers Austin Jordano at 103 and Justin Waltzer at 285, and 4th placer Joe Frank at 119 - well done, guys! |
| Tues. December 23 | New Milford | 15 | 63 |
| Sat. December 27 | Kisluk Invitational Tournament Classical Magnet |
Immaculate finishes 3rd | Congratulations to 1st place finishers Joe Frank at 119 and Gavin Buckley at 130, 2nd placers Austin Jordano at 103 and Justin Waltzer at 285, 3rd placer Andrew Cronin at 135, and 4th placer Matt Frizzell at 112 - well done, guys! |
| Tues. December 30 | Bethel | 27 | 42 |
| Sat. January 3, 2009 | Brookfield | 52 | 22 |
| Sat. January 3 | East Haven | 57 | 18 |
| Sat. January 3 | Seymour | 39 | 36 |
| Sat. January 3 | New Britain | 51 | 24 |
| Thurs. January 8 | New Fairfield | 54 | 24 |
| Sat. January 10 | Bunnell | 48 | 31 |
| Sat. January 10 | Guilford | 31 | 45 |
| Wed. January 15 | Weston | 54 | 27 |
| Tues. January 20 | Stratford | 39 | 42 |
| Wed. January 21 | Joel Barlow | 70 | 12 |
| Sat. January 24 - MUSTANG DUALS | Masuk | 36 | 40 |
| Sat. January 24 - MUSTANG DUALS | Suffield | 62 | 24 |
| Sat. January 24 - MUSTANG DUALS | Thomaston | 36 | 41 |
| Sat. January 24 - MUSTANG DUALS | Norwalk | 33 | 37 |
| Sat. January 24 - MUSTANG DUALS | Staples | 48 | 36 |
| Thurs. January 29 | Newtown | 32 | 39 |
| Sat. January 31 - Portland Duals | Portland | 60 | 24 |
| Sat. January 31 - Portland Duals | Wethersfield | 30 | 41 |
| Sat. January 31 - Portland Duals | Gilbert | 31 | 45 |
| Sat. January 31 - Portland Duals | Old Saybrook/Westbrook | 51 | 25 |