| Wed 5/2 @ TBA | Varsity Baseball Game | @ Ludlowe (Fairfield, CT)* | | - |
| Wed 5/2 @ TBA | Varsity Softball Game | vs. Ludlowe (Fairfield, CT)* | | - |
| Fri 5/4 @ 4:00 PM | Freshman Baseball Game | vs. Notre Dame Catholic (Fairfield, CT) | | - |
| Sat 5/5 @ TBA | Varsity Baseball Game | @ Warde (Fairfield, CT)* | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | @ Bassick (Bridgeport, CT)* | | - |
| Mon 5/7 @ 4:15 PM | Varsity Baseball Game | vs. Bassick (Bridgeport, CT)* | | - |
| Tue 5/8 @ TBA | Varsity Softball Game | vs. Warde (Fairfield, CT)* | | - |
| Wed 5/9 @ 4:00 PM | Freshman Baseball Game | @ Westhill (Stamford, CT) | | - |
| Wed 5/9 @ 4:00 PM | Varsity Baseball Game | vs. Westhill (Stamford, CT)* | | - |
| Wed 5/9 @ 4:00 PM | JV Baseball Game | @ Westhill (Stamford, CT) | | - |
| Thu 5/10 @ TBA | Varsity Softball Game | @ Westhill (Stamford, CT)* | | - |
| Thu 5/10 @ 4:00 PM | Freshman Baseball Game | @ Westhill (Stamford, CT) | | - |
| Thu 5/10 @ 4:30 PM | JV Baseball Game | @ Wilton (CT) | | - |
| Thu 5/10 @ 4:30 PM | Freshman Baseball Game | @ Wilton (CT) | | - |
| Thu 5/10 @ 4:30 PM | Varsity Baseball Game | vs. Wilton (CT)* | | - |
| Thu 5/10 @ 7:00 PM | Varsity Lacrosse Game | @ Ludlowe (Fairfield, CT)* | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | @ Wilton (CT)* | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | vs. Wilton (CT)* | | - |
| Fri 5/11 @ 3:00 PM | Varsity Baseball Game | vs. Wilton (CT)* | | - |
| Fri 5/11 @ 3:30 PM | JV Baseball Game | @ Wilton (CT) | | - |
| Fri 5/11 @ 3:30 PM | Freshman Baseball Game | @ Wilton (CT) | | - |
| Sat 5/12 @ TBA | Varsity Baseball Game | vs. Westhill (Stamford, CT)* | | - |
| Sat 5/12 @ 12:00 PM | JV Baseball Game | @ Westhill (Stamford, CT) | | - |
| Sat 5/12 @ 12:00 PM | Varsity Baseball Game | vs. Westhill (Stamford, CT)* | | - |
| Sat 5/12 @ 2:00 PM | Varsity Lacrosse Game | @ Darien (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Lacrosse Game | @ Westhill (Stamford, CT) | | - |
| Mon 5/14 @ 4:00 PM | Freshman Baseball Game | @ Westhill (Stamford, CT) | | - |
| Tue 5/15 @ 4:00 PM | Varsity Baseball Game | vs. Bassick (Bridgeport, CT)* | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | vs. Bridgeport Central (Bridgeport, CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Baseball Game | @ Bridgeport Central (Bridgeport, CT)* | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | vs. Bassick (Bridgeport, CT)* | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | vs. Trumbull (CT)* | | - |
| Fri 5/18 @ 4:00 PM | Varsity Baseball Game | @ Trumbull (CT)* | | - |
| Fri 5/18 @ 4:00 PM | JV Baseball Game | @ Trumbull (CT) | | - |
| Fri 5/18 @ 4:15 PM | Freshman Baseball Game | vs. Trumbull (CT) | | - |
| Tue 5/29 @ TBA | Varsity Softball Game | @ Wilcox RVT (Meriden, CT)*** | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Housatonic (Falls Village, CT)*** | | - |
| Wed 5/30 @ TBA | Varsity Softball Game | @ St. Bernard (Uncasville, CT)*** | | - |