| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Thursday | November 2, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | November 3, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Girls |
| Tuesday | November 7, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | November 9, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | November 10, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Girls |
| Tuesday | November 14, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | November 16, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | November 17, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Girls |
| Tuesday | November 21, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Tuesday | November 28, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | November 30, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | December 1, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Girls |
| Saturday | December 2, 2023 | 12:00 PM | 1:00 PM | Game | Weston High School | vs. The Basketball Schol Waterbury 5G |
| Tuesday | December 5, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | December 7, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | December 8, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Girls |
| Saturday | December 9, 2023 | 12:00 PM | 1:00 PM | Game | Weston High School | vs. Bethel 5G |
| Sunday | December 10, 2023 | 5:30 PM | 6:30 PM | Game | Newtown High | vs. Newtown Blue 5G |
| Tuesday | December 12, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | December 14, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | December 15, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Girls |
| Saturday | December 16, 2023 | 12:00 PM | 1:00 PM | Game | Weston HS Old Gym | @ Wilton 5G |
| Sunday | December 17, 2023 | 3:30 PM | 4:30 PM | Game | Long Lots Elem | @ Westport PAL Blue 5G |
| Tuesday | December 19, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | December 21, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | January 2, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | January 4, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | January 5, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Girls |
| Saturday | January 6, 2024 | 12:00 PM | 1:00 PM | Game | Weston HS Old Gym | vs. Norwalk GBA 5G |
| Saturday | January 6, 2024 | 4:00 PM | 5:00 PM | Game | Long Lots Elementary School | @ Westport PAL White 5G |
| Thursday | January 11, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | January 12, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Girls |
| Saturday | January 13, 2024 | 12:00 PM | 1:00 PM | Game | Weston HS Old Gym | vs. New Canaan 5G |
| Thursday | January 18, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | January 19, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Girls |
| Saturday | January 20, 2024 | 11:30 AM | 12:30 PM | Game | Middlebrook School | @ Wilton 5G |
| Sunday | January 21, 2024 | 11:30 AM | 12:30 PM | Game | Middlesex MS Small | @ Darien YMCA 5G |
| Tuesday | January 23, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | January 25, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | January 26, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Girls |
| Saturday | January 27, 2024 | 12:00 PM | 1:00 PM | Game | Weston HS Old Gym | vs. Stamford Youngtimers 5G |
| Sunday | January 28, 2024 | 10:15 AM | 11:15 AM | Game | Westhill High School | @ Stamford Youngtimers 5G |
| Tuesday | January 30, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | February 1, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | February 2, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Girls |
| Saturday | February 3, 2024 | 12:00 PM | 1:00 PM | Game | Weston HS Old Gym | vs. Fairfield FBA Black 5G |
| Sunday | February 4, 2024 | 1:00 PM | 2:00 PM | Game | George Washington Carver Community Center | vs. Norwalk |
| Sunday | February 4, 2024 | 1:00 PM | 2:00 PM | Game | George Washington Carver Community Center | @ Norwalk GBA 5G |
| Tuesday | February 6, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | February 8, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Saturday | February 10, 2024 | 3:00 PM | 4:00 PM | Game | Weston HS Old Gym | vs. St Theresa 5G |
| Thursday | February 15, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | February 27, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Thursday | February 29, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Sunday | March 3, 2024 | 6:25 PM | 7:45 PM | Game | Newtown YA Court 2 | vs. New Fairfield 5G |
| Tuesday | March 5, 2024 | 6:00 PM | 7:30 PM | Practice | WMS New Gym | |
| Thursday | March 7, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Sunday | March 10, 2024 | 9:30 AM | 10:50 AM | Game | Middlesex MS Large | vs. Norwalk GBA 5G |