| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Monday | October 30, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | November 1, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | November 3, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Blue, 8th Grade Boys |
| Wednesday | November 8, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | November 10, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Blue, 8th Grade Boys |
| Monday | November 13, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | November 15, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | November 17, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Blue, 8th Grade Boys |
| Monday | November 20, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Monday | November 20, 2023 | 8:45 PM | 9:00 PM | Meeting | Weston Middle School | |
| Monday | November 27, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | November 29, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | December 1, 2023 | 6:00 PM | 7:30 PM | Game | 60 Prospect St | @ Ridgefield Orange 7B |
| Saturday | December 2, 2023 | 9:00 AM | 10:30 AM | Game | Weston High School | vs. Newtown Gold 7B |
| Sunday | December 3, 2023 | 8:00 AM | 9:00 AM | Game | Foran High School | vs. Westport YMCA 7B |
| Sunday | December 3, 2023 | 1:00 PM | 2:00 PM | Game | Foran High School | @ Westport YMCA 7B |
| Monday | December 4, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | December 6, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | December 8, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Blue, 8th Grade Boys |
| Saturday | December 9, 2023 | 9:00 AM | 10:00 AM | Game | Insports Centers | vs. Stratford PAL White 7B |
| Saturday | December 9, 2023 | 1:00 PM | 2:00 PM | Game | Insports Centers | @ Stratford PAL White 7B |
| Saturday | December 9, 2023 | 4:30 PM | 6:00 PM | Game | Weston HS New Gym | vs. New Fairfield 7B |
| Sunday | December 10, 2023 | 3:00 PM | 4:00 PM | Game | Jonathan Law High School | @ Branford 7B |
| Sunday | December 10, 2023 | 5:30 PM | 6:30 PM | Game | Jonathan Law High School | vs. Branford 7B |
| Monday | December 11, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | December 13, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | December 15, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | 7th Grade Boys Blue, 8th Grade Boys |
| Saturday | December 16, 2023 | 10:00 AM | 11:00 AM | Game | Insports Centers | vs. Naugatuck Power |
| Saturday | December 16, 2023 | 2:00 PM | 3:00 PM | Game | Insports Centers | @ Naugatuck Power 7B |
| Saturday | December 16, 2023 | 4:30 PM | 6:00 PM | Game | Weston High School | vs. Westport PAL White 7B |
| Sunday | December 17, 2023 | 11:00 AM | 12:00 PM | Game | Insports Centers | @ Milford Knights Blue 7B |
| Sunday | December 17, 2023 | 2:00 PM | 3:00 PM | Game | Insports Centers | vs. Milford Knights Blue |
| Monday | December 18, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | December 20, 2023 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | January 3, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | January 5, 2024 | 6:00 PM | 7:30 PM | Extra-Practice | WMS NEW Gym | |
| Saturday | January 6, 2024 | 3:00 PM | 4:30 PM | Game | Weston HS New Gym | vs. St Marys Ridgefield 7B |
| Saturday | January 6, 2024 | 4:30 PM | 6:00 PM | Game | Weston HS New Gym | vs. Redding-Easton 7B |
| Monday | January 8, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | January 10, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | January 12, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 8th Grade Boys |
| Saturday | January 13, 2024 | 9:00 AM | 10:30 AM | Game | Weston HS Old Gym | vs. Brookfield 7B |
| Saturday | January 13, 2024 | 10:30 AM | 12:00 PM | Game | Weston HS New Gym | vs. Bethel 7B |
| Sunday | January 14, 2024 | 8:00 AM | 9:00 AM | Game | Insports Centers | vs. St Theresa |
| Sunday | January 14, 2024 | 8:00 AM | 9:00 AM | Game | @ St Theresa 7B | |
| Wednesday | January 17, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | January 19, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 8th Grade Boys |
| Saturday | January 20, 2024 | 12:30 PM | 2:00 PM | Game | NCCS Court 1 | @ New Canaan Black 7B |
| Saturday | January 20, 2024 | 3:00 PM | 4:00 PM | Game | Weston High School New Gym | vs. Westport PAL Blue 7B |
| Saturday | January 20, 2024 | 6:00 PM | 7:30 PM | Other | Milestone | |
| Sunday | January 21, 2024 | 12:00 PM | 1:00 PM | Game | Insports Centers | vs. East Haven |
| Sunday | January 21, 2024 | 12:00 PM | 1:00 PM | Game | vs. East Haven | |
| Monday | January 22, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | January 24, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | January 26, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 8th Grade Boys, 7th Grade Boys Blue |
| Saturday | January 27, 2024 | 10:30 AM | 12:00 PM | Game | Weston HS Old Gym | vs. New Milford YBA 7B |
| Saturday | January 27, 2024 | 12:00 PM | 1:30 PM | Game | Weston High School | vs. One Five Norwalk 7B |
| Sunday | January 28, 2024 | 4:30 PM | 5:30 PM | Game | Flood Middle School | vs. Go To Work |
| Sunday | January 28, 2024 | 4:30 PM | 5:30 PM | Game | 490 Chapel St | vs. Go To Work (Westport) |
| Monday | January 29, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | January 31, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | February 2, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 8th Grade Boys |
| Saturday | February 3, 2024 | 3:00 PM | 4:30 PM | Game | Weston High School | vs. Pomperaug 7B |
| Sunday | February 4, 2024 | 8:00 AM | 9:00 AM | Game | Insports Centers | vs. Another Level (Amity) |
| Sunday | February 4, 2024 | 8:00 AM | 9:00 AM | Game | Insports Centers | @ Another Level Amity |
| Sunday | February 4, 2024 | 12:00 PM | 1:30 PM | Game | Wakeman Boys & Girls Club - Smilow-Burroughs Clubhouse | @ Bridgeport Smilow 7B |
| Monday | February 5, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | February 7, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | February 9, 2024 | 6:00 PM | 7:30 PM | Practice | WMS Old Gym | 7th Grade Boys Blue, 8th Grade Boys |
| Saturday | February 10, 2024 | 2:30 PM | 3:30 PM | Game | Jonathan Law High School | vs. Another Level Basketball (Amity) |
| Saturday | February 10, 2024 | 2:30 PM | 3:30 PM | Game | Jonathan Law High School | @ Another Level Amity |
| Monday | February 12, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | February 14, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Sunday | February 25, 2024 | 12:30 PM | 2:00 PM | Game | Middlesex Middle School | @ Darien YMCA Blue 7B |
| Monday | February 26, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Wednesday | February 28, 2024 | 7:30 PM | 9:00 PM | Practice | WMS Old Gym | |
| Friday | March 1, 2024 | 6:15 PM | 7:35 PM | Game | Easton CC | vs. Bridgeport Smilow 7B |
| Saturday | March 2, 2024 | 9:50 AM | 11:10 AM | Game | Stamford JCC | @ Danbury PAL Blue 7B |
| Sunday | March 3, 2024 | 2:25 PM | 3:45 PM | Game | Yanity | @ Fairfield FBA Black 7B |
| Monday | March 4, 2024 | 4:15 PM | 5:45 PM | Practice | WHS Old Gym | |
| Wednesday | March 6, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | |
| Friday | March 8, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Sunday | March 10, 2024 | 1:00 PM | 2:20 PM | Game | Shelton Interm | @ Madison Black 7B |
| Thursday | March 21, 2024 | 6:00 PM | 7:30 PM | Other | Weston Field Club Inc |