| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Tuesday | November 14, 2023 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | November 17, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Tuesday | November 21, 2023 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Tuesday | November 28, 2023 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | December 1, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | December 2, 2023 | 5:15 PM | 6:15 PM | Game | Middlesex Middle School | @ Darien YMCA White 5B |
| Sunday | December 3, 2023 | 12:00 PM | 1:00 PM | Game | Middlebrook School | vs. New Fairfield 5B |
| Tuesday | December 5, 2023 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | December 8, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | December 9, 2023 | 8:30 AM | 9:30 AM | Game | Middlebrook School | vs. Brookfield 5B |
| Sunday | December 10, 2023 | 11:00 AM | 12:00 PM | Game | Westport YMCA | @ Westport YMCA 5B |
| Tuesday | December 12, 2023 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | December 15, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | December 16, 2023 | 11:30 AM | 12:30 PM | Game | Middlebrook School | vs. GameChangers 5B |
| Saturday | December 16, 2023 | 5:30 PM | 6:30 PM | Game | Long Lots Elementary School | @ Westport PAL White 5B |
| Tuesday | December 19, 2023 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | December 22, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Tuesday | January 2, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | January 5, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | January 6, 2024 | 2:30 PM | 3:30 PM | Game | Middlebrook School | vs. Bridgeport McGivney 6B |
| Sunday | January 7, 2024 | 9:40 AM | 10:40 AM | Game | Parsons Court 1 | @ Milford Knights Blue 5B |
| Tuesday | January 9, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | January 12, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | January 13, 2024 | 10:00 AM | 11:00 AM | Game | Middlebrook School | vs. GameChangers 5B |
| Saturday | January 13, 2024 | 1:30 PM | 2:30 PM | Game | Middlesex MS Small | @ Darien YMCA Blue 5B |
| Tuesday | January 16, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | January 19, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | January 20, 2024 | 1:00 PM | 2:00 PM | Game | Middlebrook School | vs. Westport YMCA 5B |
| Sunday | January 21, 2024 | 10:30 AM | 11:30 AM | Game | Yanity | @ Ridgefield Black 5B |
| Sunday | January 21, 2024 | 1:30 PM | 2:30 PM | Game | 60 Prospect St | @ Ridgefield Orange 5B |
| Tuesday | January 23, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | January 26, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Friday | January 26, 2024 | 6:45 PM | 7:45 PM | Game | Reed Intermed | @ Newtown Gold 5B |
| Saturday | January 27, 2024 | 1:00 PM | 2:00 PM | Game | Middlebrook MS New Gym | vs. Fairfield FBA Black 5B |
| Tuesday | January 30, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | February 2, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | February 3, 2024 | 10:00 AM | 11:00 AM | Game | Middlebrook MS New Gym | vs. One Five Norwalk 5B |
| Tuesday | February 6, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | February 9, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | February 10, 2024 | 1:00 PM | 2:00 PM | Game | Middlebrook MS Old Gym | vs. St Theresa 5B |
| Saturday | February 10, 2024 | 3:30 PM | 4:30 PM | Game | 75 3rd St | @ Greenwich Select 5B |
| Sunday | February 11, 2024 | 11:45 AM | 12:45 PM | Game | New Canaan Country School | @ New Canaan Black 5B |
| Tuesday | February 13, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | February 16, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Tuesday | February 27, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | March 1, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Saturday | March 2, 2024 | 3:40 PM | 5:00 PM | Game | Newtown YA Court 3 | vs. Shelton Black 5B |
| Tuesday | March 5, 2024 | 6:00 PM | 7:30 PM | Practice | Wilton Y Wilton YMCA | |
| Friday | March 8, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym |
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