| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Tuesday | March 26, 2024 | 6:00 PM | 7:15 PM | Practice | JTPS | Junior Boys 12U |
| Thursday | March 28, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Tuesday | April 2, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | April 4, 2024 | 7:00 PM | 8:00 PM | Practice | WHS Turf | Junior Boys 12U |
| Saturday | April 6, 2024 | 2:30 PM | 3:30 PM | Game | Lyman Hall HS | vs. @Wallingford |
| Tuesday | April 9, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | April 11, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Saturday | April 13, 2024 | 9:30 AM | 10:30 AM | Game | Schaghticoke Middle School | @ New Milford |
| Sunday | April 14, 2024 | 9:15 AM | 10:30 AM | Game | WHS Turf | vs. vs Monroe |
| Tuesday | April 16, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | April 18, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Sunday | April 21, 2024 | 10:30 AM | 11:45 AM | Game | WHS Turf | vs. vs New Milford |
| Tuesday | April 23, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | April 25, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Saturday | April 27, 2024 | 1:00 PM | 2:15 PM | Game | Watertown High School | vs. Newtown |
| Tuesday | April 30, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | May 2, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Sunday | May 5, 2024 | 9:15 AM | 10:30 AM | Game | WHS Turf | vs. vs Litchfield |
| Tuesday | May 7, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | May 9, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Saturday | May 11, 2024 | 3:00 PM | 4:00 PM | Game | Masuk HS | vs. @ Monroe |
| Sunday | May 12, 2024 | 10:30 AM | 11:45 AM | Game | WHS Turf | vs. vs Bethel |
| Tuesday | May 14, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Tuesday | May 14, 2024 | 6:15 PM | 6:30 PM | Other | John Trumbull Primary School | |
| Thursday | May 16, 2024 | 6:00 PM | 7:15 PM | Practice | JTPS | |
| Saturday | May 18, 2024 | 9:00 AM | 10:00 AM | Game | Bethel High School | @ Bethel |
| Sunday | May 19, 2024 | 11:45 AM | 2:45 PM | Game | Newtown High School | @ CONNY Tournament |
| Tuesday | May 21, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | May 23, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Monday | May 27, 2024 | 8:45 AM | 10:45 AM | Other | Watertown Plaza | |
| Tuesday | May 28, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | May 30, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Saturday | June 1, 2024 | 10:00 AM | 11:15 AM | Game | Settlers Park | vs. @ Pomperaug |
| Tuesday | June 4, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Thursday | June 6, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Sunday | June 9, 2024 | 12:30 PM | 1:45 PM | Game | Swift Middle School | vs. Wallingford |
| Tuesday | June 11, 2024 | 6:00 PM | 7:15 PM | Game | Bantam Civic Association | @ Litchfield |
| Tuesday | June 11, 2024 | 6:00 PM | 7:15 PM | Game | JTPS | vs. Practice |
| Sunday | June 30, 2024 | 1:00 PM | 4:00 PM | Other | The Lopez Homestead |