| Wed 5/2 @ TBA | Varsity Softball Game | @ Bridgeport Central (Bridgeport, CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Baseball Game | vs. Bridgeport Central (Bridgeport, CT)* | | - |
| Fri 5/4 @ 4:00 PM | Varsity Boys Volleyball Game | @ Darien (CT)F | | - |
| Sat 5/5 @ 12:00 PM | Varsity Baseball Game | @ Bassick (Bridgeport, CT)** | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | vs. Ludlowe (Fairfield, CT)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Baseball Game | @ Ludlowe (Fairfield, CT)* | | - |
| Wed 5/9 @ 4:00 PM | Varsity Baseball Game | @ Norwalk (CT)* | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | vs. McMahon (Norwalk, CT)* | | - |
| Fri 5/11 @ 4:00 PM | Varsity Baseball Game | @ McMahon (Norwalk, CT)* | | - |
| Sat 5/12 @ TBA | Varsity Baseball Game | @ Norwalk (CT)* | | - |
| Sat 5/12 @ TBA | Varsity Softball Game | vs. Norwalk (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | @ Trumbull (CT)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Boys Volleyball Game | @ Staples (Westport, CT)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Baseball Game | vs. Trumbull (CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Softball Game | vs. New Canaan (CT)* | | - |
| Wed 5/16 @ 4:00 PM | JV Baseball Game | @ New Canaan (CT) | | - |
| Wed 5/16 @ 4:00 PM | Varsity Baseball Game | @ New Canaan (CT)* | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | @ Stamford (CT)* | | - |
| Fri 5/18 @ 4:00 PM | Varsity Baseball Game | vs. Stamford (CT)* | | - |
| Mon 5/21 @ TBA | Varsity Softball Game | vs. Stratford (CT) | | - |
| Tue 5/22 @ TBA | Varsity Softball Game | @ McMahon (Norwalk, CT)* | | - |