| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Friday | November 10, 2023 | 7:30 PM | 8:30 PM | Game | Insports Centers | vs. Monroe Red Storm 6B |
| Monday | November 13, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | November 17, 2023 | 5:30 PM | 6:30 PM | Game | Insports Centers | @ Milford Knights White 6B |
| Friday | November 17, 2023 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | November 18, 2023 | 2:00 PM | 3:00 PM | Game | Insports Centers | @ Fairfield FBA Blue 6B |
| Monday | November 20, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Monday | November 27, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | December 1, 2023 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | December 2, 2023 | 2:30 PM | 3:30 PM | Game | Middlebrook MS New Gym | vs. Fairfield FBA Blue 6B |
| Sunday | December 3, 2023 | 4:30 PM | 5:30 PM | Game | Middlebrook MS Old Gym | vs. New Canaan Red 6B |
| Monday | December 4, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | December 8, 2023 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | December 9, 2023 | 4:00 PM | 5:00 PM | Game | Middlebrook MS New Gym | @ Bridgeport Smilow 5/6B |
| Sunday | December 10, 2023 | 1:30 PM | 2:30 PM | Game | Middlebrook School | vs. Bethel 6B |
| Monday | December 11, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | December 15, 2023 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | December 16, 2023 | 10:00 AM | 11:00 AM | Game | Middlebrook School | vs. Fairfield FBA Black 6B |
| Monday | December 18, 2023 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | December 22, 2023 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Friday | January 5, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | January 6, 2024 | 3:45 PM | 4:45 PM | Game | New Canaan Country School | @ New Canaan Red 6B |
| Monday | January 8, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | January 12, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | January 13, 2024 | 1:30 PM | 2:30 PM | Game | Carver Center | @ Norwalk Youth Carver 6B |
| Sunday | January 14, 2024 | 3:00 PM | 4:00 PM | Game | Middlebrook School | vs. Danbury PAL 6B |
| Friday | January 19, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | January 20, 2024 | 2:30 PM | 3:30 PM | Game | Middlebrook School | vs. Fairfield FBA Blue 6B |
| Sunday | January 21, 2024 | 3:15 PM | 4:30 PM | Game | Middlesex Middle School | @ Darien YMCA 6B White |
| Monday | January 22, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | January 26, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | January 27, 2024 | 10:00 AM | 11:00 AM | Game | Middlebrook MS New Gym | vs. Darien YMCA White 6B |
| Saturday | January 27, 2024 | 4:15 PM | 5:15 PM | Game | Shelton Interm | @ Shelton Black 6B |
| Sunday | January 28, 2024 | 12:00 PM | 1:00 PM | Game | Middlebrook School | vs. OFB |
| Sunday | January 28, 2024 | 3:00 PM | 4:00 PM | Game | Middlebrook MS New Gym | vs. Westport PAL White 6B |
| Monday | January 29, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | February 2, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | February 3, 2024 | 11:30 AM | 12:30 PM | Game | Middlebrook MS New Gym | vs. Fairfield FBA Red 6B |
| Sunday | February 4, 2024 | 12:00 PM | 1:00 PM | Game | Middlebrook School | vs. Bethel 6B |
| Monday | February 5, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | February 9, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | February 10, 2024 | 4:00 PM | 5:00 PM | Game | Middlebrook MS New Gym | @ St Mark 5/6B |
| Sunday | February 11, 2024 | 10:30 AM | 11:30 AM | Game | Middlebrook School | vs. Weston |
| Sunday | February 11, 2024 | 12:00 PM | 1:00 PM | Game | Middlebrook MS New Gym | vs. Ridgefield Black 6B |
| Monday | February 12, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | February 16, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Saturday | February 17, 2024 | 1:30 PM | 2:30 PM | Game | George Washington Carver Community Center | @ Norwalk Youth Carver 6B |
| Monday | February 26, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | March 1, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym | |
| Friday | March 1, 2024 | 8:55 PM | 10:15 PM | Game | Easton CC | @ Newtown Gold 6B |
| Monday | March 4, 2024 | 6:00 PM | 7:30 PM | Practice | Cider Mill Lower Gym | |
| Friday | March 8, 2024 | 6:00 PM | 7:30 PM | Practice | Middlebrook New Gym |
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