| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Monday | November 13, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | November 15, 2023 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Monday | November 20, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Monday | November 27, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | November 29, 2023 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Friday | December 1, 2023 | 6:30 PM | 7:30 PM | Game | Whisconier Middle School | @ Brookfield 8B |
| Saturday | December 2, 2023 | 12:30 PM | 1:30 PM | Game | Police Athletic League Inc. | @ Danbury PAL White 8B |
| Sunday | December 3, 2023 | 1:30 PM | 2:30 PM | Game | Middlebrook School | vs. Weston Gold 8B |
| Monday | December 4, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | December 6, 2023 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Saturday | December 9, 2023 | 6:15 PM | 7:15 PM | Game | Parsons Full Court | @ Milford Knights White 8B |
| Sunday | December 10, 2023 | 3:00 PM | 4:00 PM | Game | Middlebrook School | vs. Bridge Academy 8B |
| Monday | December 11, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | December 13, 2023 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Saturday | December 16, 2023 | 4:15 PM | 5:15 PM | Game | New Canaan Country School | @ New Canaan Red 8B |
| Sunday | December 17, 2023 | 3:00 PM | 4:00 PM | Game | Middlebrook MS Old Gym | vs. Bridgeport McGivney 8B |
| Monday | December 18, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | December 20, 2023 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | January 3, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Monday | January 8, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | January 10, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Saturday | January 13, 2024 | 3:30 PM | 4:30 PM | Game | Hall House BPT | @ Bridgeport Kings Kids 8B |
| Sunday | January 14, 2024 | 12:00 PM | 1:00 PM | Game | Middlebrook School | vs. Shelton Orange 8B |
| Wednesday | January 17, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Saturday | January 20, 2024 | 3:00 PM | 4:00 PM | Game | Wakeman-Southp | @ Wakeman - Southport 8B |
| Sunday | January 21, 2024 | 1:30 PM | 2:30 PM | Game | Middlebrook MS New Gym | vs. Fairfield FBA Red 8B |
| Monday | January 22, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | January 24, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Saturday | January 27, 2024 | 2:30 PM | 3:30 PM | Game | Middlebrook MS New Gym | vs. Bridgeport MAC-Caribe 8B |
| Sunday | January 28, 2024 | 1:30 PM | 2:30 PM | Game | Middlebrook School | vs. Fairfield FBA Red 8B |
| Monday | January 29, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | January 31, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Friday | February 2, 2024 | 7:00 PM | 8:00 PM | Game | Western MS | @ Greenwich Boys and Girls 8B |
| Saturday | February 3, 2024 | 1:00 PM | 2:00 PM | Game | Middlebrook MS New Gym | @ Westport PAL Gold 8B |
| Sunday | February 4, 2024 | 1:30 PM | 2:30 PM | Game | Middlebrook MS New Gym | vs. Bridge Academy Panthers 8B |
| Monday | February 5, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | February 7, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Friday | February 9, 2024 | 7:00 PM | 8:00 PM | Other | WHS Field House | |
| Friday | February 9, 2024 | 7:00 PM | 8:00 PM | Other | WHS Field House | |
| Saturday | February 10, 2024 | 8:00 PM | 9:00 PM | Game | Stamford JCC | @ Stamford JCC White 8B |
| Sunday | February 11, 2024 | 1:30 PM | 2:30 PM | Game | Middlebrook School | vs. Ridgefield Oranhe 8B |
| Monday | February 12, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | February 14, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Monday | February 26, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | February 28, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym | |
| Thursday | February 29, 2024 | 6:30 PM | 7:50 PM | Game | Yanity | @ Stamford JCC White 8B |
| Monday | March 4, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Upper Gym | |
| Wednesday | March 6, 2024 | 7:30 PM | 9:00 PM | Practice | Cider Mill Upper Gym |
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