| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | November 1, 2023 | 7:00 PM | 8:30 PM | Meeting | Weston Middle School | |
| Monday | November 6, 2023 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Thursday | November 9, 2023 | 7:00 PM | 8:15 PM | Practice | St. Ann | |
| Monday | November 13, 2023 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Friday | November 17, 2023 | 7:30 PM | 8:45 PM | Practice | RLMS Court A | |
| Saturday | November 18, 2023 | 11:00 AM | 12:30 PM | Game | Yanity Gym | @ Ridgefield Black |
| Monday | November 20, 2023 | 5:30 PM | 6:45 PM | Practice | RLMS Court B | |
| Monday | November 27, 2023 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Friday | December 1, 2023 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | December 2, 2023 | 11:50 AM | 1:20 PM | Game | Parsons gymnasium | @ Milford White |
| Saturday | December 2, 2023 | 4:15 PM | 5:45 PM | Game | Saxe Middle School | @ New Canaan White |
| Sunday | December 3, 2023 | 3:15 PM | 4:45 PM | Game | St. Ann Church | vs. New Fairfield Blue |
| Monday | December 4, 2023 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Thursday | December 7, 2023 | 5:30 PM | 6:45 PM | Other | Roger Ludlowe Middle School | |
| Friday | December 8, 2023 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | December 9, 2023 | 4:30 PM | 6:00 PM | Game | Weston High School | @ Weston Blue |
| Sunday | December 10, 2023 | 3:45 PM | 5:15 PM | Game | Rochambeau Middle School | @ Pomperaug |
| Monday | December 11, 2023 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Friday | December 15, 2023 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | December 16, 2023 | 3:15 PM | 4:45 PM | Game | St. Ann Church | vs. Ridgefield Orange |
| Sunday | December 17, 2023 | 1:30 PM | 3:00 PM | Game | Brookfield High School | @ Brookfield |
| Monday | December 18, 2023 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Wednesday | December 20, 2023 | 6:00 PM | 7:30 PM | Other | Wakeman Boys & Girls Club - Southport Clubhouse | |
| Saturday | December 23, 2023 | 2:00 PM | 3:30 PM | Game | Wakeman Boys & Girls Club - Smilow-Burroughs Clubhouse | @ Bridgeport Smilow |
| Thursday | January 4, 2024 | 7:00 PM | 8:00 PM | Practice | RLMS Small Gym | |
| Friday | January 5, 2024 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | January 6, 2024 | 4:20 PM | 5:20 PM | Game | Mohegan Sun | @ Bristol Warren Wolfpack RI - Mohegan Sun Tournament |
| Saturday | January 6, 2024 | 6:00 PM | 7:00 PM | Game | Mohegan Sun | @ Waterford CT - Mohegan Sun Tournament |
| Sunday | January 7, 2024 | 2:40 PM | 3:40 PM | Game | Mohegan Sun | @ Paramus Spartans NJ MOHEGAN SUN TOURNAMENT |
| Sunday | January 7, 2024 | 5:10 PM | 6:10 PM | Game | Mohegan Sun | @ Branford CT MOHEGAN SUN TOURAMENT |
| Monday | January 8, 2024 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Friday | January 12, 2024 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | January 13, 2024 | 4:30 PM | 6:00 PM | Game | St. Ann Church | vs. Milford White |
| Sunday | January 14, 2024 | 3:15 PM | 4:45 PM | Game | St. Ann Church | vs. Shelton Black |
| Tuesday | January 16, 2024 | 6:15 PM | 7:30 PM | Practice | McKinley | 6B Black |
| Friday | January 19, 2024 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | January 20, 2024 | 5:45 PM | 7:15 PM | Game | St. Ann Church | vs. Monroe Red Storm |
| Sunday | January 21, 2024 | 6:15 PM | 7:45 PM | Game | Canterbury Field House | @ New Milford |
| Monday | January 22, 2024 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Friday | January 26, 2024 | 7:00 PM | 8:30 PM | Game | Westport Weston Family YMCA | @ Westport YMCA 5 A |
| Friday | January 26, 2024 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | January 27, 2024 | 10:15 AM | 11:45 AM | Game | St. Ann Church | vs. Fairfield Red |
| Saturday | January 27, 2024 | 4:30 PM | 6:00 PM | Game | Frank Scott Bunnell High School | @ Seymour Travel |
| Sunday | January 28, 2024 | 10:00 AM | 11:30 AM | Game | Hamden Middle School | @ Hamden |
| Sunday | January 28, 2024 | 2:30 PM | 4:00 PM | Game | Flood Middle School | @ Stratford PAL Blue |
| Monday | January 29, 2024 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Friday | February 2, 2024 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | February 3, 2024 | 1:15 PM | 2:45 PM | Game | Wakeman Boys & Girls Club - Madison Avenue Community Clubhouse | @ Bridgeport MAC Caribe |
| Sunday | February 4, 2024 | 1:00 PM | 2:30 PM | Game | Police Athletic League Inc. | @ Danbury PAL |
| Sunday | February 4, 2024 | 6:00 PM | 7:30 PM | Game | Redding Recreation Department | @ Redding / Easton |
| Monday | February 5, 2024 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Friday | February 9, 2024 | 7:30 PM | 8:45 PM | Practice | RLMS Court B | |
| Saturday | February 10, 2024 | 3:00 PM | 4:30 PM | Game | Wakeman Boys & Girls Club - Southport Clubhouse | @ Wakeman / Southport |
| Sunday | February 11, 2024 | 1:00 PM | 2:30 PM | Game | New Fairfield High School | @ New Fairfield Red |
| Monday | February 12, 2024 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Wednesday | February 14, 2024 | 6:00 PM | 7:00 PM | Practice | RLMS Small Gym | |
| Tuesday | February 20, 2024 | 8:00 PM | 9:00 PM | Practice | RLMS Small Gym | |
| Tuesday | February 20, 2024 | 8:40 PM | 9:00 PM | Other | RLMS Small Gym | |
| Friday | February 23, 2024 | 8:00 PM | 9:15 PM | Practice | Woods Court B | |
| Saturday | February 24, 2024 | 4:45 PM | 6:15 PM | Game | High Rise Basketball | @ Greenwich Select |
| Sunday | February 25, 2024 | 1:00 PM | 2:00 PM | Game | Insports Centers | @ CT Hoopfest Playoff Monroe Red Storm |
| Sunday | February 25, 2024 | 3:00 PM | 4:30 PM | Game | Middlesex Middle School | @ Darien White |
| Monday | February 26, 2024 | 6:45 PM | 8:00 PM | Practice | RLMS Court A | |
| Wednesday | February 28, 2024 | 8:00 PM | 9:00 PM | Practice | RLMS Small Gym | |
| Friday | March 1, 2024 | 6:00 PM | 7:30 PM | Game | Saxe Middle School | @ FBCL Play in Game Playoffs Bridgeport MAC CARIBE |
| Sunday | March 3, 2024 | 8:00 AM | 9:30 AM | Game | Insports Centers | @ CT Hoopfest Madison Gold |
| Thursday | March 7, 2024 | 5:30 PM | 6:45 PM | Practice | Woods Court B | |
| Friday | March 8, 2024 | 6:15 PM | 7:30 PM | Practice | RLMS Court B | |
| Saturday | March 9, 2024 | 2:00 PM | 3:30 PM | Game | Insports Centers | @ CT Hoopfest Quarterfinals Monroe Red Storm |
| Saturday | March 9, 2024 | 4:00 PM | 5:30 PM | Game | Insports Centers | @ CT Hoopfest Semifinals vs Winner of East Haven |