| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Thursday | November 2, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | November 3, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Boys Gold, 6th Grade Boys Blue |
| Tuesday | November 7, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | November 9, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | November 10, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Boys Gold, 6th Grade Boys Blue |
| Saturday | November 11, 2023 | 10:00 AM | 11:00 AM | Game | Insports Centers | @ Newtown |
| Sunday | November 12, 2023 | 6:00 PM | 7:00 PM | Game | Parsons Complex | @ Milford Knights |
| Tuesday | November 14, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | November 16, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | November 16, 2023 | 7:30 PM | 7:45 PM | Meeting | Weston Intermediate School | |
| Friday | November 17, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Boys Gold, 6th Grade Boys Blue |
| Saturday | November 18, 2023 | 1:15 PM | 2:15 PM | Game | Parsons Complex | vs. St Theresa 5B |
| Saturday | November 18, 2023 | 1:15 PM | 2:15 PM | Game | Parsons Complex | @ St Theresa’s |
| Tuesday | November 21, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Tuesday | November 28, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | November 30, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | December 1, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Boys Gold, 6th Grade Boys Blue |
| Friday | December 1, 2023 | 6:45 PM | 7:45 PM | Game | Reed Intermed | @ Newtown Blue 5B |
| Saturday | December 2, 2023 | 1:30 PM | 2:30 PM | Game | Weston HS Old Gym | vs. New Canaan Red Chargers 5B |
| Sunday | December 3, 2023 | 10:00 AM | 11:00 AM | Game | Insports Centers | @ FBA Fairfield Blue |
| Sunday | December 3, 2023 | 12:00 PM | 1:00 PM | Game | Insports Centers | @ Fairfield FBA Blue 5B |
| Tuesday | December 5, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | December 7, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | December 8, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Boys Gold, 6th Grade Boys Blue |
| Friday | December 8, 2023 | 6:30 PM | 7:30 PM | Game | Long Lots Elem | @ Westport PAL Blue 5B |
| Saturday | December 9, 2023 | 9:00 AM | 10:00 AM | Game | Weston HS New Gym | vs. New Fairfield 5B |
| Saturday | December 9, 2023 | 12:00 PM | 1:00 PM | Game | Insports Centers | @ St Theresa 5B |
| Saturday | December 9, 2023 | 1:00 PM | 2:00 PM | Game | Insports Centers | @ St. Theresa's |
| Sunday | December 10, 2023 | 8:00 AM | 9:00 AM | Game | Insports Centers | @ Stratford PAL Blue |
| Sunday | December 10, 2023 | 12:00 PM | 1:00 PM | Game | Insports Centers | @ Stratford PAL Blue 5B |
| Tuesday | December 12, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | December 14, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | December 15, 2023 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Boys Gold, 6th Grade Boys Blue |
| Saturday | December 16, 2023 | 2:00 PM | 3:00 PM | Game | Frank Scott Bunnell High School | @ Dribble Drive Orangemen 5B |
| Saturday | December 16, 2023 | 5:30 PM | 6:30 PM | Game | Frank Scott Bunnell High School | @ Dribble Drive Orangemen |
| Sunday | December 17, 2023 | 11:00 AM | 12:00 PM | Game | Insports Centers | @ Stratford PAL White |
| Sunday | December 17, 2023 | 2:00 PM | 3:00 PM | Game | Insports Centers | @ Stratford PAL White 5B |
| Tuesday | December 19, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | December 21, 2023 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Tuesday | January 2, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | January 4, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | January 5, 2024 | 4:30 PM | 6:00 PM | Practice | WIS | 6th Grade Boys Gold, 6th Grade Boys Blue |
| Saturday | January 6, 2024 | 1:30 PM | 2:30 PM | Game | Weston HS New Gym | vs. Danbury PAL 5B |
| Thursday | January 11, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | January 12, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Boys Blue, 6th Grade Boys Gold |
| Saturday | January 13, 2024 | 9:00 AM | 10:00 AM | Game | Weston HS Old Gym | vs. Fairfield FBA Blue 5B |
| Saturday | January 13, 2024 | 1:30 PM | 2:30 PM | Game | Weston HS New Gym | vs. Mt. Vernon Jr. Knights 5B |
| Sunday | January 14, 2024 | 11:00 AM | 12:00 PM | Game | Insports Centers | @ REBA |
| Sunday | January 14, 2024 | 2:30 PM | 3:30 PM | Game | NCCS Court 2 | @ New Canaan Black Rams 5B |
| Thursday | January 18, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | January 19, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Boys Blue, 6th Grade Boys Gold |
| Saturday | January 20, 2024 | 1:30 PM | 2:30 PM | Game | Weston HS Old Gym | vs. Wakeman-Southport Blue 5B |
| Saturday | January 20, 2024 | 5:30 PM | 6:30 PM | Game | Frank Scott Bunnell High School | @ Milford Knights Blue |
| Sunday | January 21, 2024 | 10:00 AM | 11:00 AM | Game | Insports Centers | @ Monroe Parks and Rec |
| Tuesday | January 23, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | January 25, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | January 26, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Boys Blue, 6th Grade Boys Gold |
| Saturday | January 27, 2024 | 1:30 PM | 2:30 PM | Game | Weston HS Old Gym | vs. Orangemen 5B |
| Sunday | January 28, 2024 | 12:00 PM | 1:00 PM | Game | Insports Centers | @ Milford Knights White |
| Sunday | January 28, 2024 | 2:00 PM | 3:00 PM | Game | Insports Centers | vs. Milford Knights White 5B |
| Tuesday | January 30, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | February 1, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | February 2, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Boys Blue, 6th Grade Boys Gold |
| Sunday | February 4, 2024 | 10:00 AM | 11:00 AM | Game | Insports Centers | @ Monroe Park and Rec |
| Tuesday | February 6, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | February 8, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | February 9, 2024 | 4:30 PM | 6:00 PM | Practice | WMS Old Gym | 6th Grade Boys Blue, 6th Grade Boys Gold |
| Saturday | February 10, 2024 | 5:30 PM | 6:30 PM | Game | Flood Middle School | @ Milford Playoffs |
| Sunday | February 11, 2024 | 10:00 AM | 11:00 AM | Game | Insports Centers | @ FBA Boys Blue |
| Thursday | February 15, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Sunday | February 25, 2024 | 5:30 PM | 6:30 PM | Game | Parsons Complex | @ St. Theresas |
| Tuesday | February 27, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | February 29, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Friday | March 1, 2024 | 6:15 PM | 7:35 PM | Game | Stamford JCC | vs. New Canaan Red Chargers 5B |
| Sunday | March 3, 2024 | 10:00 AM | 11:00 AM | Game | Parsons Complex | @ Branford |
| Tuesday | March 5, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Thursday | March 7, 2024 | 6:00 PM | 7:30 PM | Practice | WIS | |
| Saturday | March 9, 2024 | 6:30 PM | 7:30 PM | Game | Frank Scott Bunnell High School | @ FBA Red |