| Wed 5/2 @ TBA | Varsity Softball Game | @ Litchfield (CT)* | | - |
| Wed 5/2 @ 3:45 PM | Varsity Baseball Game | vs. Litchfield (CT)* | | - |
| Thu 5/3 @ TBA | Varsity Softball Game | vs. Northwestern Regional (Winsted, CT)* | | - |
| Fri 5/4 @ TBA | Varsity Softball Game | @ Ellington (CT) | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | @ Lewis Mills (Burlington, CT)* | | - |
| Mon 5/7 @ 3:45 PM | Varsity Baseball Game | vs. Lewis Mills (Burlington, CT)* | | - |
| Wed 5/9 @ TBA | Varsity Softball Game | vs. Shepaug Valley (Washington, CT)* | | - |
| Wed 5/9 @ 3:45 PM | Varsity Baseball Game | @ Shepaug Valley (Washington, CT)* | | - |
| Thu 5/10 @ 3:45 PM | Varsity Baseball Game | @ Wamogo Regional (Litchfield, CT)* | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | vs. Wamogo (Litchfield, CT) | | - |
| Mon 5/14 @ 3:45 PM | Varsity Baseball Game | @ Norwich RVT (Norwich, CT) | | - |
| Wed 5/16 @ 3:45 PM | Varsity Baseball Game | @ Housatonic (Falls Village, CT)* | | - |
| Wed 5/16 @ 3:45 PM | Varsity Softball Game | vs. Housatonic (Falls Village, CT)* | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | @ Northwestern Regional (Winsted, CT)* | | - |
| Sat 5/19 @ 11:00 AM | Varsity Baseball Game | vs. Northwestern Regional (Winsted, CT)* | | - |
| Mon 5/21 @ TBA | Varsity Softball Game | vs. Terryville (CT)* | | - |
| Mon 5/21 @ 3:45 PM | Varsity Baseball Game | @ Terryville (CT)* | | - |
| Tue 5/22 @ 4:00 PM | Varsity Softball Game | @ Nonnewaug (Woodbury, CT)* | | - |
| Wed 5/23 @ 3:45 PM | Varsity Baseball Game | vs. Nonnewaug (Woodbury, CT)* | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Immaculate (Danbury, CT)*** | | - |
| Wed 5/30 @ 3:30 PM | Varsity Baseball Game | vs. TBA*** | | - |