| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Thursday | November 2, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | November 3, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Gold, 7th Grade Boys Blue |
| Thursday | November 9, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | November 10, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Gold, 7th Grade Boys Blue |
| Tuesday | November 14, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | November 16, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | November 17, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Gold, 7th Grade Boys Blue |
| Tuesday | November 21, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Tuesday | November 28, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | November 30, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | December 1, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Blue |
| Saturday | December 2, 2023 | 1:30 PM | 2:30 PM | Game | Weston High School | vs. Fairfield FBA Red 8B |
| Sunday | December 3, 2023 | 1:30 PM | 2:30 PM | Game | Middlebrook School | @ Wilton White 8B |
| Tuesday | December 5, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | December 7, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | December 8, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Gold, 7th Grade Boys Blue |
| Saturday | December 9, 2023 | 9:00 AM | 10:00 AM | Game | Weston HS New Gym | vs. Monroe Park and Rec 8B |
| Sunday | December 10, 2023 | 1:30 PM | 2:30 PM | Game | Newtown High | @ Newtown Blue 8B |
| Tuesday | December 12, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | December 14, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | December 15, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Gold, 7th Grade Boys Blue |
| Saturday | December 16, 2023 | 6:00 PM | 7:00 PM | Game | Weston HS New Gym | vs. St Marys Ridgefield 8B |
| Tuesday | December 19, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | December 21, 2023 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | January 4, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 5, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Blue |
| Saturday | January 6, 2024 | 9:00 AM | 10:00 AM | Game | Weston HS New Gym | vs. Bethel 8B |
| Saturday | January 6, 2024 | 5:00 PM | 6:00 PM | Game | Yanity | @ Ridgefield Orange 8B |
| Thursday | January 11, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 12, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 7th Grade Boys Gold |
| Saturday | January 13, 2024 | 7:30 PM | 8:30 PM | Game | Weston HS New Gym | vs. Danbury PAL White 8B |
| Sunday | January 14, 2024 | 4:00 PM | 5:00 PM | Game | Wakeman Boys & Girls Club - Southport Clubhouse | @ Wakeman Southport 8B |
| Thursday | January 18, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 19, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 7th Grade Boys Gold |
| Saturday | January 20, 2024 | 12:00 PM | 1:00 PM | Game | Weston HS New Gym | vs. New Fairfield Red 8B |
| Tuesday | January 23, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | January 25, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | January 26, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 7th Grade Boys Gold |
| Saturday | January 27, 2024 | 12:00 PM | 1:00 PM | Game | Westport Weston Family YMCA | vs. Westport PAL Gold 8B |
| Saturday | January 27, 2024 | 12:00 PM | 1:00 PM | Game | Westport Weston Family YMCA | @ Westport PAL Gold |
| Saturday | January 27, 2024 | 4:30 PM | 5:30 PM | Game | Weston HS Old Gym | vs. Brookfield 8B |
| Thursday | February 1, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | February 2, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 7th Grade Boys Gold |
| Saturday | February 3, 2024 | 12:00 PM | 1:00 PM | Game | St. Mary School | @ St Mary 8B |
| Saturday | February 3, 2024 | 3:00 PM | 4:00 PM | Game | Weston Intermediate School | @ Ridgefield Orange 8B |
| Sunday | February 4, 2024 | 5:00 PM | 6:00 PM | Game | Wakeman Boys & Girls Club - Madison Avenue Community Clubhouse | @ Bridgeport MAC Caribe 8B |
| Tuesday | February 6, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | February 8, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | February 9, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 7th Grade Boys Gold |
| Saturday | February 10, 2024 | 12:30 PM | 1:30 PM | Game | Shelton Interm | @ Shelton Orange 8B |
| Saturday | February 10, 2024 | 7:30 PM | 8:30 PM | Game | Weston High School | vs. Wakeman Southport 8B |
| Thursday | February 15, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Sunday | February 25, 2024 | 4:30 PM | 12:30 AM | Other | Milford | |
| Tuesday | February 27, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | February 29, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Friday | March 1, 2024 | 6:30 PM | 7:50 PM | Game | St Mary School | vs. New Fairfield Red 8B |
| Saturday | March 2, 2024 | 2:50 PM | 3:50 PM | Game | Easton Community Center | vs. Shelton |
| Saturday | March 2, 2024 | 2:50 PM | 4:10 PM | Game | Easton CC | @ Shelton Orange 8B |
| Sunday | March 3, 2024 | 5:30 PM | 6:30 PM | Game | Jonathan Law High School | vs. Newtown Bkue |
| Tuesday | March 5, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | |
| Thursday | March 7, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym |