| Tue 5/1 @ 4:00 PM | Varsity Lacrosse Game | @ Notre Dame Catholic (Fairfield, CT) | | - |
| Tue 5/1 @ 4:00 PM | Varsity Girls Lacrosse Game | @ St. Joseph (Trumbull, CT) | | - |
| Wed 5/2 @ 4:15 PM | Varsity Softball Game | vs. Barlow (Redding, CT)* | | - |
| Wed 5/2 @ 7:00 PM | Varsity Girls Lacrosse Game | @ West Haven (CT) | | - |
| Thu 5/3 @ 6:30 PM | Varsity Softball Game | vs. Kolbe-Cathedral (Bridgeport, CT)* | | - |
| Fri 5/4 @ 5:30 PM | Varsity Girls Lacrosse Game | vs. Lauralton Hall (Milford, CT)* | | - |
| Sat 5/5 @ 3:00 PM | Varsity Baseball Game | @ Immaculate (Danbury, CT)* | | - |
| Sat 5/5 @ 3:00 PM | Varsity Lacrosse Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Mon 5/7 @ 4:15 PM | Varsity Baseball Game | @ New Fairfield (CT)* | | - |
| Mon 5/7 @ 4:15 PM | Varsity Softball Game | @ New Fairfield (CT)* | | - |
| Tue 5/8 @ 5:30 PM | Varsity Lacrosse Game | @ Brookfield (CT)* | | - |
| Tue 5/8 @ 5:30 PM | Varsity Girls Lacrosse Game | @ New Fairfield (CT)* | | - |
| Wed 5/9 @ 4:15 PM | Varsity Softball Game | vs. Pomperaug (Southbury, CT)* | | - |
| Wed 5/9 @ 7:00 PM | Varsity Lacrosse Game | vs. Weston (CT)* | | - |
| Thu 5/10 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Newtown (CT)* | | - |
| Sat 5/12 @ 1:00 PM | Varsity Baseball Game | @ Bunnell (Stratford, CT)* | | - |
| Sat 5/12 @ 1:00 PM | Varsity Girls Lacrosse Game | @ Notre Dame Catholic (Fairfield, CT) | | - |
| Sat 5/12 @ 7:00 PM | Varsity Softball Game | @ Bunnell (Stratford, CT)* | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | @ Newtown (CT)* | | - |
| Mon 5/14 @ 4:15 PM | Varsity Baseball Game | @ Newtown (CT)* | | - |
| Tue 5/15 @ 4:00 PM | Varsity Girls Lacrosse Game | @ New Milford (CT)* | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | vs. Masuk (Monroe, CT)* | | - |
| Wed 5/16 @ 7:00 PM | Varsity Lacrosse Game | @ Newtown (CT)* | | - |
| Thu 5/17 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Immaculate (Danbury, CT)* | | - |
| Thu 5/17 @ 4:15 PM | Varsity Baseball Game | vs. Barlow (Redding, CT)* | | - |
| Thu 5/17 @ 7:00 PM | Varsity Baseball Game | @ Barlow (Redding, CT) | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | vs. Immaculate (Danbury, CT)* | | - |
| Fri 5/18 @ 4:15 PM | Varsity Baseball Game | vs. Pomperaug (Southbury, CT)* | | - |
| Fri 5/18 @ 7:00 PM | Varsity Lacrosse Game | @ West Haven (CT) | | - |
| Sat 5/19 @ 1:30 PM | Varsity Baseball Game | vs. Masuk (Monroe, CT)* | | - |
| Sat 5/19 @ 4:30 PM | Varsity Girls Lacrosse Game | vs. Bunnell (Stratford, CT) | | - |
| Sat 5/19 @ 7:00 PM | Varsity Lacrosse Game | @ Bunnell (Stratford, CT) | | - |
| Mon 5/21 @ TBA | Varsity Softball Game | @ Harding (Bridgeport, CT) | | - |
| Mon 5/21 @ 4:00 PM | Varsity Lacrosse Game | @ Wilbur Cross (New Haven, CT) | | - |
| Tue 5/22 @ TBA | Varsity Softball Game | @ Immaculate (Danbury, CT)* | | - |
| Tue 5/22 @ 3:15 PM | Varsity Baseball Game | @ Newtown (CT)*** | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Foran (Milford, CT)** | | - |