| Tue 5/1 @ 4:00 PM | JV Baseball Game | vs. Barlow (Redding, CT) | | - |
| Tue 5/1 @ 4:30 PM | Varsity Softball Game | @ Weston (CT) | | - |
| Tue 5/1 @ 5:00 PM | Varsity Girls Lacrosse Game | @ Bethel (CT)* | | - |
| Tue 5/1 @ 5:30 PM | Varsity Boys Volleyball Game | @ Xavier (Middletown, CT) | | - |
| Wed 5/2 @ 3:45 PM | JV Baseball Game | vs. Barlow (Redding, CT) | | - |
| Wed 5/2 @ 4:15 PM | Varsity Baseball Game | vs. Bunnell (Stratford, CT)* | | - |
| Wed 5/2 @ 4:15 PM | Varsity Softball Game | vs. Bunnell (Stratford, CT)* | | - |
| Thu 5/3 @ 4:00 PM | Varsity Lacrosse Game | vs. Newtown (CT)* | | - |
| Thu 5/3 @ 5:30 PM | Varsity Boys Volleyball Game | vs. Lewis Mills (Burlington, CT) | | - |
| Fri 5/4 @ TBA | Varsity Baseball Game | @ Pomperaug (Southbury, CT)* | | - |
| Fri 5/4 @ 4:15 PM | Varsity Softball Game | @ Pomperaug (Southbury, CT)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Lacrosse Game | vs. St. Joseph (Trumbull, CT) | | - |
| Mon 5/7 @ 4:15 PM | Varsity Baseball Game | @ Oxford (CT) | | - |
| Mon 5/7 @ 5:30 PM | Varsity Boys Volleyball Game | @ Kolbe-Cathedral (Bridgeport, CT)* | | - |
| Tue 5/8 @ 4:30 PM | Varsity Lacrosse Game | vs. Housatonic (Falls Village, CT) | | - |
| Wed 5/9 @ TBA | Varsity Softball Game | vs. Newtown (CT)* | | - |
| Wed 5/9 @ 6:00 PM | Varsity Baseball Game | @ Newtown (CT)* | | - |
| Thu 5/10 @ 3:45 PM | JV Baseball Game | vs. Newtown (CT) | | - |
| Thu 5/10 @ 4:00 PM | JV Baseball Game | vs. Newtown (CT) | | - |
| Thu 5/10 @ 7:00 PM | Varsity Boys Volleyball Game | @ Shelton (CT) | | - |
| Thu 5/10 @ 7:00 PM | Varsity Lacrosse Game | @ Pomperaug (Southbury, CT)* | | - |
| Fri 5/11 @ 3:45 PM | JV Baseball Game | @ New Milford (CT) | | - |
| Fri 5/11 @ 4:15 PM | Varsity Softball Game | vs. New Milford (CT)* | | - |
| Fri 5/11 @ 4:15 PM | Varsity Baseball Game | vs. New Milford (CT)* | | - |
| Fri 5/11 @ 5:30 PM | Varsity Boys Volleyball Game | @ Lewis Mills (Burlington, CT) | | - |
| Sat 5/12 @ 3:00 PM | Varsity Softball Game | @ Lauralton Hall (Milford, CT)* | | - |
| Mon 5/14 @ TBA | Varsity Girls Lacrosse Game | vs. Pomperaug (Southbury, CT) | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | vs. Brookfield (CT)* | | - |
| Mon 5/14 @ 4:15 PM | Varsity Baseball Game | vs. Brookfield (CT)* | | - |
| Mon 5/14 @ 5:30 PM | Varsity Boys Volleyball Game | vs. Barlow (Redding, CT)* | | - |
| Tue 5/15 @ 7:00 PM | Varsity Lacrosse Game | vs. Bethel (CT)* | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | @ Stratford (CT)* | | - |
| Wed 5/16 @ 3:45 PM | Freshman Baseball Game | vs. Newtown (CT) | | - |
| Wed 5/16 @ 4:00 PM | Varsity Boys Volleyball Game | @ Oxford (CT)* | | - |
| Thu 5/17 @ TBA | Varsity Softball Game | @ Brookfield (CT)* | | - |
| Thu 5/17 @ 4:15 PM | Varsity Baseball Game | @ New Fairfield (CT) | | - |
| Thu 5/17 @ 5:30 PM | Varsity Boys Volleyball Game | vs. Ridgefield (CT) | | - |
| Thu 5/17 @ 7:00 PM | Varsity Girls Lacrosse Game | vs. Newtown (CT)* | | - |
| Fri 5/18 @ 4:00 PM | Varsity Lacrosse Game | @ Notre Dame Catholic (Fairfield, CT)* | | - |
| Sat 5/19 @ 11:00 AM | Varsity Lacrosse Game | vs. Westhill (Stamford, CT) | | - |
| Sat 5/19 @ 1:30 PM | Varsity Baseball Game | @ Stratford (CT)* | | - |
| Mon 5/21 @ 3:45 PM | JV Softball Game | @ New Milford (CT) | | - |
| Thu 5/24 @ 4:15 PM | Varsity Softball Game | @ Lauralton Hall (Milford, CT)* | | - |
| Tue 5/29 @ TBA | Varsity Softball Game | @ Staples (Westport, CT)*** | | - |
| Wed 5/30 @ TBA | Varsity Softball Game | @ Cheshire (CT)*** | | - |