| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Friday | August 29, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Tuesday | September 2, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Thursday | September 4, 2025 | 4:00 PM | 5:30 PM | Extra-Practice | Bible Street Park | |
| Thursday | September 4, 2025 | 5:30 PM | 6:30 PM | Other | Bible Street Park | |
| Friday | September 5, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Sunday | September 7, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. Mavericks |
| Tuesday | September 9, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Friday | September 12, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Sunday | September 14, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. Raiders |
| Tuesday | September 16, 2025 | 4:00 PM | 5:00 PM | Extra-Practice | Bible Street Park | |
| Friday | September 19, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Saturday | September 20, 2025 | 7:45 AM | 9:00 AM | Other | Cos Cob School | |
| Saturday | September 20, 2025 | 1:00 PM | 3:00 PM | Other | Greenwich High School | |
| Sunday | September 21, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. Generals |
| Tuesday | September 23, 2025 | 3:30 PM | 5:00 PM | Extra-Practice | Bible Street Park | |
| Friday | September 26, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Friday | September 26, 2025 | 6:00 PM | 7:00 PM | Other | Bible Street Park | |
| Tuesday | September 30, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Tuesday | September 30, 2025 | 4:00 PM | 4:30 PM | Other | Bible Street Park | |
| Thursday | October 2, 2025 | 3:00 PM | 4:30 PM | Extra-Practice | Bible Street Park | |
| Friday | October 3, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Sunday | October 5, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. Generals |
| Tuesday | October 7, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Friday | October 10, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Sunday | October 12, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. Mavericks |
| Tuesday | October 14, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Friday | October 17, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Sunday | October 19, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. Bulldogs |
| Tuesday | October 21, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Wednesday | October 22, 2025 | 2:00 PM | 4:00 PM | Extra-Practice | Bible Street Park | |
| Friday | October 24, 2025 | 4:00 PM | 6:00 PM | Extra-Practice | Bible Street Park | |
| Saturday | October 25, 2025 | 10:00 AM | 12:00 PM | Extra-Practice | Cos Cob School | |
| Saturday | October 25, 2025 | 11:50 AM | 12:05 PM | Other | Cos Cob School | |
| Sunday | October 26, 2025 | 5:00 PM | 7:00 PM | Other | Greenwich High School | |
| Tuesday | October 28, 2025 | 4:00 PM | 5:30 PM | Extra-Practice | Bible Street Park | |
| Sunday | November 2, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. Raiders |
| Tuesday | November 4, 2025 | 4:00 PM | 5:00 PM | Extra-Practice | Bible Street Park | |
| Sunday | November 9, 2025 | 11:30 AM | 1:30 PM | Game | Greenwich High School | vs. TBD |
| Friday | November 14, 2025 | 4:00 PM | 5:00 PM | Extra-Practice | Bible Street Park | |
| Sunday | November 16, 2025 | TBD | TBD | Game | Greenwich High School | vs. TBD |
| Sunday | November 30, 2025 | 5:00 PM | 9:00 PM | Other | Hyatt Regency Greenwich |