| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Monday | October 30, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | November 1, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | November 3, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Gold |
| Monday | November 6, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | November 8, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | November 10, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Gold |
| Monday | November 13, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | November 15, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | November 17, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Gold |
| Monday | November 20, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Monday | November 27, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | November 29, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | December 1, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | December 2, 2023 | 9:00 AM | 10:00 AM | Game | Weston HS New Gym | vs. Milford Knights White 6B |
| Sunday | December 3, 2023 | 3:45 PM | 4:45 PM | Game | New Canaan Country School | @ New Canaan White 6B |
| Monday | December 4, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | December 6, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | December 8, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | December 9, 2023 | 4:30 PM | 5:30 PM | Game | Weston HS Old Gym | vs. Fairfield FBA Yellow 6B |
| Sunday | December 10, 2023 | 1:30 PM | 2:30 PM | Game | Brookfield HS Small Gym | @ Brookfield 6B |
| Monday | December 11, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | December 13, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | December 15, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | December 16, 2023 | 3:00 PM | 4:00 PM | Game | Weston HS New Gym | vs. New Milford YBA 6B |
| Monday | December 18, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | December 20, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Wednesday | January 3, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 5, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Gold |
| Sunday | January 7, 2024 | 12:00 PM | 1:00 PM | Game | Yanity | @ Ridgefield Orange 6B |
| Monday | January 8, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | January 10, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 12, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | January 13, 2024 | 10:30 AM | 11:30 AM | Game | Weston High School | vs. Bridgeport MAC-Caribe 6B |
| Wednesday | January 17, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 19, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | January 20, 2024 | 3:00 PM | 4:00 PM | Game | Weston HS New Gym | vs. Monroe Red Storm 6B |
| Monday | January 22, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | January 24, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 26, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | January 27, 2024 | 9:00 AM | 10:00 AM | Game | Weston High School | vs. Ridgefield Orange 6B |
| Sunday | January 28, 2024 | 3:00 PM | 4:00 PM | Game | Newtown High | @ Newtown Blue 6B |
| Monday | January 29, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | January 31, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | February 2, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | February 3, 2024 | 6:00 PM | 7:00 PM | Game | Weston High School | vs. Brookfield 6B |
| Sunday | February 4, 2024 | 6:15 PM | 7:15 PM | Game | Canterbury School | @ New Milford 6B |
| Monday | February 5, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | February 7, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | February 9, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Gold |
| Saturday | February 10, 2024 | 4:45 PM | 5:45 PM | Game | NFairfield HS New Gym | @ New Fairfield Blue 6B |
| Monday | February 12, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | February 14, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Monday | February 26, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Wednesday | February 28, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | February 29, 2024 | 7:35 PM | 8:55 PM | Game | Stamford JCC | vs. United Youth-Norwalk 6B |
| Saturday | March 2, 2024 | 12:00 PM | 1:00 PM | Other | Foran High School | |
| Sunday | March 3, 2024 | 8:00 AM | 9:00 AM | Other | Insports Centers | |
| Monday | March 4, 2024 | 6:00 PM | 7:30 PM | Practice | WIS |