| Tue 5/1 @ 4:30 PM | Varsity Lacrosse Game | @ Valley Regional (Deep River, CT) | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | @ Mount Everett Regional (Sheffield, MA) | | - |
| Wed 5/2 @ 3:45 PM | Varsity Softball Game | vs. Wolcott RVT (Torrington, CT) | | - |
| Thu 5/3 @ 4:30 PM | Varsity Girls Lacrosse Game | vs. Lewis Mills (Burlington, CT)* | | - |
| Fri 5/4 @ TBA | Varsity Softball Game | @ Northwestern Regional (Winsted, CT)* | | - |
| Fri 5/4 @ 3:45 PM | Varsity Baseball Game | vs. Northwestern Regional (Winsted, CT)* | | - |
| Mon 5/7 @ 3:45 PM | Varsity Softball Game | vs. Terryville (CT)* | | - |
| Mon 5/7 @ 3:45 PM | Varsity Baseball Game | @ Terryville (CT)* | | - |
| Tue 5/8 @ 4:30 PM | Varsity Lacrosse Game | @ Masuk (Monroe, CT) | | - |
| Thu 5/10 @ 3:45 AM | Varsity Softball Game | @ Nonnewaug (Woodbury, CT)* | | - |
| Thu 5/10 @ 3:45 PM | Varsity Baseball Game | vs. Nonnewaug (Woodbury, CT)* | | - |
| Thu 5/10 @ 4:45 PM | Varsity Lacrosse Game | vs. Farmington (CT) | | - |
| Fri 5/11 @ 3:15 PM | Varsity Softball Game | vs. Thomaston (CT)* | | - |
| Fri 5/11 @ 3:45 PM | Varsity Baseball Game | vs. Thomaston (CT)* | | - |
| Sat 5/12 @ 12:00 PM | Varsity Lacrosse Game | vs. Nonnewaug (Woodbury, CT)* | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | @ Litchfield (CT)* | | - |
| Mon 5/14 @ 3:45 PM | Varsity Softball Game | vs. Litchfield (CT)* | | - |
| Wed 5/16 @ 3:45 PM | Varsity Baseball Game | vs. Gilbert (Winsted, CT)* | | - |
| Wed 5/16 @ 3:45 PM | Varsity Softball Game | @ Gilbert (Winsted, CT)* | | - |
| Wed 5/16 @ 7:00 PM | Varsity Girls Lacrosse Game | @ Watertown (CT)* | | - |
| Fri 5/18 @ TBA | Varsity Baseball Game | @ Lewis Mills (Burlington, CT)* | | - |
| Fri 5/18 @ 3:45 PM | Varsity Softball Game | vs. Lewis Mills (Burlington, CT)* | | - |
| Mon 5/21 @ 3:45 PM | Varsity Softball Game | vs. Shepaug Valley (Washington, CT)* | | - |
| Mon 5/21 @ 3:45 PM | Varsity Baseball Game | @ Shepaug Valley (Washington, CT)* | | - |
| Tue 5/22 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Bacon Academy (Colchester, CT) | | - |
| Tue 5/22 @ 6:00 PM | Varsity Lacrosse Game | @ Farmington (CT) | | - |
| Wed 5/23 @ TBA | Varsity Softball Game | @ Wamogo Regional (Litchfield, CT)* | | - |
| Wed 5/23 @ 3:45 PM | Varsity Baseball Game | vs. Wamogo Regional (Litchfield, CT)* | | - |
| Sat 5/26 @ 11:00 AM | Varsity Girls Lacrosse Game | @ Lewis Mills (Burlington, CT)* | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Trinity Catholic (Stamford, CT)*** | | - |
| Tue 5/29 @ 5:00 PM | Varsity Girls Lacrosse Game | @ Lewis Mills (Burlington, CT)** | | - |