| Tue 5/1 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Stamford (CT) | | - |
| Wed 5/2 @ TBA | Varsity Softball Game | vs. Danbury (CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Baseball Game | @ Danbury (CT)* | | - |
| Wed 5/2 @ 6:30 PM | Varsity Lacrosse Game | @ Staples (Westport, CT)* | | - |
| Fri 5/4 @ TBA | Varsity Softball Game | @ Staples (Westport, CT)* | | - |
| Fri 5/4 @ TBA | Varsity Baseball Game | vs. Staples (Westport, CT)* | | - |
| Sat 5/5 @ 5:00 PM | Varsity Lacrosse Game | vs. Shelton (CT) | | - |
| Mon 5/7 @ 4:00 PM | Varsity Softball Game | vs. St. Joseph (Trumbull, CT)* | | - |
| Mon 5/7 @ 4:15 PM | Varsity Baseball Game | @ St. Joseph (Trumbull, CT)* | | - |
| Tue 5/8 @ 4:00 PM | Varsity Lacrosse Game | vs. Ludlowe (Fairfield, CT)* | | - |
| Wed 5/9 @ 4:00 PM | Freshman Baseball Game | vs. Trinity Catholic (Stamford, CT) | | - |
| Wed 5/9 @ 4:00 PM | Varsity Baseball Game | @ Trinity Catholic (Stamford, CT)* | | - |
| Wed 5/9 @ 4:00 PM | JV Baseball Game | vs. Trinity Catholic (Stamford, CT) | | - |
| Thu 5/10 @ TBA | Varsity Softball Game | vs. Trinity Catholic (Stamford, CT)* | | - |
| Thu 5/10 @ 4:00 PM | Freshman Baseball Game | vs. Trinity Catholic (Stamford, CT) | | - |
| Thu 5/10 @ 7:00 PM | Varsity Lacrosse Game | @ Warde (Fairfield, CT)* | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | vs. New Canaan (CT)* | | - |
| Fri 5/11 @ 4:00 PM | Varsity Softball Game | @ New Canaan (CT)* | | - |
| Fri 5/11 @ 4:00 PM | Freshman Baseball Game | @ New Canaan (CT) | | - |
| Sat 5/12 @ TBA | Varsity Baseball Game | @ Trinity Catholic (Stamford, CT)* | | - |
| Sat 5/12 @ 11:00 AM | Varsity Lacrosse Game | vs. McMahon (Norwalk, CT)* | | - |
| Sat 5/12 @ 12:00 PM | JV Baseball Game | vs. Trinity Catholic (Stamford, CT) | | - |
| Sat 5/12 @ 12:00 PM | Varsity Baseball Game | @ Trinity Catholic (Stamford, CT)* | | - |
| Sat 5/12 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Ridgefield (CT) | | - |
| Mon 5/14 @ TBA | Varsity Lacrosse Game | vs. Trinity Catholic (Stamford, CT) | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | vs. Norwalk (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | @ Norwalk (CT)* | | - |
| Mon 5/14 @ 4:00 PM | Freshman Baseball Game | vs. Trinity Catholic (Stamford, CT) | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | @ Wilton (CT)* | | - |
| Wed 5/16 @ 4:30 PM | JV Baseball Game | vs. Wilton (CT) | | - |
| Wed 5/16 @ 4:30 PM | Varsity Baseball Game | vs. Wilton (CT)* | | - |
| Wed 5/16 @ 5:00 PM | Varsity Lacrosse Game | @ Greenwich (CT)* | | - |
| Thu 5/17 @ TBA | Varsity Softball Game | @ Ridgefield (CT)* | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | vs. Ridgefield (CT)* | | - |
| Thu 5/17 @ 4:00 PM | Varsity Softball Game | @ Ridgefield (CT)* | | - |
| Sat 5/19 @ 11:00 AM | Varsity Lacrosse Game | @ Masuk (Monroe, CT) | | - |
| Mon 5/21 @ 6:00 PM | Varsity Girls Lacrosse Game | vs. Lewis Mills (Burlington, CT) | | - |
| Tue 5/29 @ TBA | Varsity Softball Game | @ Warde (Fairfield, CT)*** | | - |
| Wed 5/30 @ TBA | Varsity Softball Game | @ Naugatuck (CT)*** | | - |