| Tue 5/1 @ TBA | Varsity Lacrosse Game | @ Danbury (CT)* | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | @ New Canaan (CT)* | | - |
| Wed 5/2 @ 3:45 PM | Varsity Softball Game | vs. New Canaan (CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Stamford (CT)* | | - |
| Fri 5/4 @ 7:00 PM | Varsity Lacrosse Game | vs. Bunnell (Stratford, CT) | | - |
| Sat 5/5 @ TBA | Varsity Baseball Game | vs. Trinity Catholic (Stamford, CT)* | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | vs. Bridgeport Central (Bridgeport, CT)* | | - |
| Mon 5/7 @ TBA | Varsity Lacrosse Game | @ Wilton (CT)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Baseball Game | @ Bridgeport Central (Bridgeport, CT)* | | - |
| Tue 5/8 @ TBA | Varsity Softball Game | @ Trinity Catholic (Stamford, CT)* | | - |
| Wed 5/9 @ 4:00 PM | Varsity Softball Game | vs. Ridgefield (CT)* | | - |
| Thu 5/10 @ TBA | Varsity Baseball Game | @ Ridgefield (CT)* | | - |
| Thu 5/10 @ TBA | Varsity Softball Game | vs. Ridgefield (CT)* | | - |
| Thu 5/10 @ 7:00 PM | Varsity Lacrosse Game | vs. Westhill (Stamford, CT)* | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | @ Darien (CT)* | | - |
| Fri 5/11 @ 3:45 PM | Varsity Baseball Game | vs. Darien (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | vs. Stamford (CT)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Baseball Game | @ Stamford (CT)* | | - |
| Tue 5/15 @ 7:00 PM | Varsity Lacrosse Game | @ Ludlowe (Fairfield, CT)* | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | @ Greenwich (CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Baseball Game | vs. Greenwich (CT)* | | - |
| Thu 5/17 @ 7:00 PM | Varsity Girls Lacrosse Game | vs. Bethel (CT) | | - |
| Fri 5/18 @ 3:45 PM | Varsity Baseball Game | vs. St. Joseph (Trumbull, CT)* | | - |
| Fri 5/18 @ 4:00 PM | Varsity Softball Game | @ St. Joseph (Trumbull, CT)* | | - |
| Wed 5/23 @ 7:00 PM | Varsity Lacrosse Game | @ Berlin (CT) | | - |
| Fri 5/25 @ TBA | Varsity Lacrosse Game | @ Notre Dame (West Haven, CT)** | | - |
| Wed 5/30 @ TBA | Varsity Lacrosse Game | @ East Lyme (CT)** | | - |