| Tue 5/1 @ 4:00 PM | Varsity Lacrosse Game | vs. Stratford (CT) | | - |
| Wed 5/2 @ TBA | Varsity Softball Game | vs. Oxford (CT)* | | - |
| Wed 5/2 @ 4:15 PM | Varsity Baseball Game | vs. Oxford (CT)* | | - |
| Thu 5/3 @ 3:45 PM | JV Baseball Game | @ Oxford (CT)* | | - |
| Fri 5/4 @ 4:00 PM | Freshman Baseball Game | @ Trinity Catholic (Stamford, CT) | | - |
| Sat 5/5 @ 11:00 AM | JV Baseball Game | vs. Kolbe (Bridgeport, CT)* | | - |
| Sat 5/5 @ 3:15 PM | Varsity Baseball Game | @ Bunnell (Stratford, CT) | | - |
| Mon 5/7 @ TBA | Varsity Girls Lacrosse Game | @ Pomperaug (Southbury, CT) | | - |
| Mon 5/7 @ 4:15 PM | Varsity Baseball Game | @ Weston (CT)* | | - |
| Tue 5/8 @ TBA | Varsity Softball Game | @ Kolbe-Cathedral (Bridgeport, CT)* | | - |
| Tue 5/8 @ 3:45 PM | JV Baseball Game | vs. Weston (CT)* | | - |
| Wed 5/9 @ TBA | Varsity Lacrosse Game | @ New Milford (CT)* | | - |
| Wed 5/9 @ 4:00 PM | Freshman Baseball Game | vs. Ridgefield (CT) | | - |
| Fri 5/11 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Barlow (Redding, CT)* | | - |
| Fri 5/11 @ 4:15 PM | Varsity Baseball Game | @ Barlow (Redding, CT)* | | - |
| Fri 5/11 @ 4:15 PM | Varsity Softball Game | @ Barlow (Redding, CT)* | | - |
| Sat 5/12 @ 10:00 AM | JV Baseball Game | vs. Barlow (Redding, CT)* | | - |
| Sat 5/12 @ 12:00 PM | Varsity Lacrosse Game | vs. Watertown (CT) | | - |
| Sat 5/12 @ 1:00 PM | Varsity Girls Lacrosse Game | vs. Stratford (CT) | | - |
| Sat 5/12 @ 3:00 PM | Varsity Baseball Game | @ Brookfield (CT)* | | - |
| Sat 5/12 @ 10:00 PM | Varsity Softball Game | vs. Weston (CT)* | | - |
| Mon 5/14 @ 4:15 PM | Varsity Baseball Game | @ Pomperaug (Southbury, CT) | | - |
| Tue 5/15 @ TBA | Varsity Softball Game | @ Brookfield (CT)* | | - |
| Tue 5/15 @ 4:00 PM | Varsity Lacrosse Game | @ New Fairfield (CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Softball Game | @ Weston (CT) | | - |
| Wed 5/16 @ 4:15 PM | Varsity Softball Game | vs. New Fairfield (CT)* | | - |
| Thu 5/17 @ 3:45 PM | JV Baseball Game | @ Barlow (Redding, CT)* | | - |
| Thu 5/17 @ 4:00 PM | Varsity Lacrosse Game | vs. West Haven (CT) | | - |
| Thu 5/17 @ 5:00 PM | Freshman Baseball Game | @ Greenwich (CT) | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | vs. Kolbe-Cathedral (Bridgeport, CT)* | | - |
| Fri 5/18 @ 3:45 PM | JV Baseball Game | @ New Fairfield (CT)* | | - |
| Fri 5/18 @ 4:00 PM | Varsity Lacrosse Game | vs. Masuk (Monroe, CT)* | | - |
| Fri 5/18 @ 4:00 PM | Freshman Baseball Game | @ St. Joseph (Trumbull, CT) | | - |
| Fri 5/18 @ 4:15 PM | Varsity Baseball Game | vs. New Fairfield (CT)* | | - |
| Fri 5/18 @ 4:45 PM | Varsity Softball Game | @ Weston (CT) | | - |
| Sat 5/19 @ 3:00 PM | Varsity Baseball Game | vs. Immaculate (Danbury, CT)* | | - |
| Sat 5/19 @ 5:00 PM | Varsity Girls Lacrosse Game | vs. Watertown (CT) | | - |
| Mon 5/21 @ TBA | Varsity Softball Game | vs. Immaculate (Danbury, CT)* | | - |