| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | November 1, 2023 | 7:00 PM | 8:00 PM | Meeting | Weston Middle School | |
| Monday | November 6, 2023 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | November 9, 2023 | 6:45 PM | 8:00 PM | Practice | RLMS Court B | |
| Monday | November 13, 2023 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | November 16, 2023 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Monday | November 20, 2023 | 4:30 PM | 5:30 PM | Practice | St. Ann | 5B Black |
| Monday | November 27, 2023 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | November 30, 2023 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Saturday | December 2, 2023 | 3:15 PM | 4:15 PM | Game | St Ann Church | vs. Westport PAL Blue 5B |
| Sunday | December 3, 2023 | 2:00 PM | 3:00 PM | Game | Insports Centers | @ Weston Gold 5B |
| Sunday | December 3, 2023 | 4:15 PM | 5:15 PM | Game | NCCS Court 1 | @ New Canaan Red Chargers 5B |
| Monday | December 4, 2023 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | December 7, 2023 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Saturday | December 9, 2023 | 2:00 PM | 3:00 PM | Game | St Ann Church | vs. Wakeman-Southport Blue 5B |
| Sunday | December 10, 2023 | 9:00 AM | 10:00 AM | Game | Insports Centers | vs. Milford Knights White |
| Sunday | December 10, 2023 | 2:00 PM | 3:00 PM | Game | Insports Centers | @ Milford Knights Blue 5B |
| Thursday | December 14, 2023 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Saturday | December 16, 2023 | 12:45 PM | 1:45 PM | Game | St Ann Church | vs. Newtown Blue 5B |
| Sunday | December 17, 2023 | 4:00 PM | 5:00 PM | Game | Insports Centers | @ Stratford PAL Blue 5B |
| Monday | December 18, 2023 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | December 21, 2023 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Wednesday | January 3, 2024 | 6:00 PM | 7:00 PM | Practice | RLMS Small Gym | |
| Thursday | January 4, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Saturday | January 6, 2024 | 1:00 PM | 2:00 PM | Game | Mohegan Sun | @ Madison Gold 5B |
| Saturday | January 6, 2024 | 2:40 PM | 3:40 PM | Game | Mohegan Sun | @ Paramus NJ 5B |
| Sunday | January 7, 2024 | 8:00 AM | 9:00 AM | Game | Mohegan Sun | @ Shelton Black 5B |
| Monday | January 8, 2024 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | January 11, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Saturday | January 13, 2024 | 9:00 AM | 10:00 AM | Game | Weston HS Old Gym | @ Weston Gold 5B |
| Saturday | January 13, 2024 | 2:00 PM | 3:00 PM | Game | St Ann Church | vs. New Canaan Black Rams 5B |
| Sunday | January 14, 2024 | 9:00 AM | 10:00 AM | Game | Insports Centers | vs. Dribble Drive Orangeman |
| Sunday | January 14, 2024 | 11:30 AM | 12:30 PM | Game | St Ann Church | vs. Orangemen 5B |
| Sunday | January 14, 2024 | 7:00 PM | 8:00 PM | Game | St Ann Church | vs. Danbury PAL 5B |
| Monday | January 15, 2024 | 5:00 PM | 6:00 PM | Practice | St. Ann | |
| Thursday | January 18, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | 5B Red |
| Sunday | January 21, 2024 | 2:00 PM | 3:00 PM | Game | Insports Centers | @ Milford Knights White 5B |
| Monday | January 22, 2024 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Wednesday | January 24, 2024 | 7:00 PM | 8:00 PM | Game | N.Fairfield MS | @ New Fairfield 5B |
| Thursday | January 25, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Sunday | January 28, 2024 | 10:00 AM | 11:00 AM | Game | Insports Centers | vs. Monroe |
| Sunday | January 28, 2024 | 7:00 PM | 8:00 PM | Game | St Ann Church | vs. Mt. Vernon Jr. Knights 5B |
| Monday | January 29, 2024 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | February 1, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Sunday | February 4, 2024 | 3:00 PM | 4:00 PM | Game | Wakeman Boys & Girls Club - Southport Clubhouse | @ Wakeman-Southport Blue 5B |
| Monday | February 5, 2024 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | February 8, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Saturday | February 10, 2024 | 12:30 PM | 1:30 PM | Game | Foran High School | @ REBA |
| Sunday | February 11, 2024 | 10:00 AM | 11:00 AM | Game | Insports Centers | @ TBD |
| Monday | February 12, 2024 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | February 15, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Tuesday | February 20, 2024 | 6:00 PM | 7:00 PM | Practice | RLMS Small Gym | |
| Thursday | February 22, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Monday | February 26, 2024 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | February 29, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann | |
| Saturday | March 2, 2024 | 1:30 PM | 2:50 PM | Game | Saxe MS Small Gym | @ Mt. Vernon Jr. Knights 5B |
| Monday | March 4, 2024 | 4:30 PM | 5:45 PM | Practice | St. Ann | |
| Thursday | March 7, 2024 | 5:45 PM | 7:00 PM | Practice | St. Ann |