| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Monday | October 30, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | November 3, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Blue |
| Wednesday | November 8, 2023 | 6:00 PM | 7:30 PM | Extra-Practice | WMS- Old Gym | |
| Friday | November 10, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Blue |
| Monday | November 13, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | November 14, 2023 | 6:00 PM | 7:30 PM | Extra-Practice | WIS | |
| Friday | November 17, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Blue |
| Monday | November 20, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | November 21, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Monday | November 27, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | November 28, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | December 1, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | December 2, 2023 | 10:30 AM | 11:30 AM | Game | Weston HS Old Gym | vs. Pomperaug 6B |
| Sunday | December 3, 2023 | 10:00 AM | 11:00 AM | Game | Hamden MS | @ Hamden Fathers 6B |
| Monday | December 4, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | December 5, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | December 8, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | December 9, 2023 | 3:00 PM | 4:00 PM | Game | Weston HS Old Gym | vs. Bethel 6B |
| Monday | December 11, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | December 12, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | December 15, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | December 16, 2023 | 1:30 PM | 2:30 PM | Game | Weston High School | vs. Norwalk 6B |
| Saturday | December 16, 2023 | 1:30 PM | 2:30 PM | Game | Weston High School | vs. Norwak |
| Sunday | December 17, 2023 | 1:00 PM | 2:00 PM | Game | NFairfield HS Old Gym | @ New Fairfield Red 6B |
| Monday | December 18, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | December 19, 2023 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | January 2, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | January 5, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | January 6, 2024 | 9:00 AM | 10:00 AM | Game | Weston High School | vs. New Fairfield Red 6B |
| Sunday | January 7, 2024 | 9:00 AM | 10:00 AM | Game | Rochambeau Middle School | @ Pomperaug 6B |
| Monday | January 8, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | January 12, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | January 13, 2024 | 12:00 AM | 1:00 AM | Game | Weston High School | vs. Naugatuck Power 6B |
| Sunday | January 14, 2024 | 9:10 AM | 10:10 AM | Game | Branford Rec | @ Branford Hornets 6B |
| Friday | January 19, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | January 20, 2024 | 4:30 PM | 5:30 PM | Game | Weston HS Old Gym | vs. Redding-Easton 6B |
| Sunday | January 21, 2024 | 1:00 PM | 2:00 PM | Game | Danbury PAL Court 1 | @ Danbury PAL 6B |
| Monday | January 22, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | January 23, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | January 26, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Blue |
| Friday | January 26, 2024 | 7:30 PM | 8:30 PM | Game | Yanity Gym | @ Ridgefield Black 6B |
| Saturday | January 27, 2024 | 2:30 PM | 3:30 PM | Game | Helen Keller Middle School | @ Redding-Easton 6B |
| Sunday | January 28, 2024 | 4:15 PM | 5:15 PM | Game | New Canaan Country School | @ New Canaan Red 6B |
| Monday | January 29, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | January 30, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | February 2, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | February 3, 2024 | 4:30 PM | 5:30 PM | Game | Weston High School | vs. Branford Hornets 6B |
| Sunday | February 4, 2024 | 9:00 AM | 10:00 AM | Game | Clifford J. Hurgin Municipal Center | @ Bethel 6B |
| Monday | February 5, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | February 6, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Friday | February 9, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 5th Grade Boys, 6th Grade Boys Blue |
| Saturday | February 10, 2024 | 12:00 PM | 1:00 PM | Game | Torrington Arm | @ Torrington PAL 6B |
| Sunday | February 11, 2024 | 10:45 AM | 11:45 AM | Game | Wilton | @ Wilton / Middlebrook Middle school New Gym |
| Monday | February 12, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Saturday | February 17, 2024 | 3:00 PM | 4:00 PM | Game | Weston HS New Gym | vs. Waterbury PAL 6B |
| Sunday | February 25, 2024 | 1:30 PM | 2:30 PM | Game | Jonathan Law High School | vs. Seymour in Milford |
| Monday | February 26, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | February 27, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Saturday | March 2, 2024 | 1:00 PM | 2:00 PM | Game | 80 Foran Rd | vs. Milford Lakers |
| Saturday | March 2, 2024 | 4:10 PM | 5:30 PM | Game | Saxe MS Small Gym | vs. United Youth-Norwalk 6B |
| Sunday | March 3, 2024 | 7:20 PM | 8:20 PM | Game | Westhill High School | vs. Brookfield 6B |
| Sunday | March 3, 2024 | 7:20 PM | 8:40 PM | Game | Westhill HS Main Gym | vs. Brookfield 6B |
| Monday | March 4, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Tuesday | March 5, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | |
| Saturday | March 9, 2024 | 4:30 PM | 5:30 PM | Game | Frank Scott Bunnell High School | vs. Stratford PAL Blue 6B |
| Saturday | March 16, 2024 | 11:00 AM | 7:00 PM | Other | The Kartrite Resort & Indoor Waterpark |