| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Tuesday | August 25, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | August 28, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | August 28, 2026 | 5:30 PM | 6:00 PM | Other | Bible Street Park | |
| Monday | August 31, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Tuesday | September 1, 2026 | 6:15 PM | 7:15 PM | Extra-Practice | International School at Dundee | |
| Tuesday | September 1, 2026 | 7:15 PM | 7:30 PM | Meeting | International School at Dundee | |
| Wednesday | September 2, 2026 | 4:15 PM | 5:15 PM | Extra-Practice | Bibl | |
| Wednesday | September 2, 2026 | 5:15 PM | 7:00 PM | Other | Bible Street Park | |
| Thursday | September 3, 2026 | 6:15 PM | 7:15 PM | Game | Greenwich High School | vs. Raiders (Away) |
| Tuesday | September 8, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | September 10, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | September 11, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Tuesday | September 15, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | September 17, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | September 18, 2026 | 3:45 PM | 5:45 PM | Extra-Practice | Bible Street Park | |
| Saturday | September 19, 2026 | 1:00 PM | 2:00 PM | Other | New Lebanon School | |
| Sunday | September 20, 2026 | 1:30 PM | 3:00 PM | Game | Greenwich High School | vs. Bulldogs |
| Tuesday | September 22, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | September 24, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | September 25, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Tuesday | September 29, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | October 1, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | October 2, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Sunday | October 4, 2026 | 1:30 PM | 3:00 PM | Game | Greenwich High School | vs. Bulldogs |
| Tuesday | October 6, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | October 8, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | October 9, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | October 9, 2026 | 4:00 PM | 4:30 PM | Other | Bible Street Park | |
| Sunday | October 11, 2026 | 1:30 PM | 3:00 PM | Game | Greenwich High School | vs. Raiders |
| Tuesday | October 13, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | October 15, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | October 16, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Sunday | October 18, 2026 | 1:30 PM | 3:00 PM | Game | Greenwich High School | vs. Generals |
| Tuesday | October 20, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | October 22, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Saturday | October 24, 2026 | 9:30 AM | 11:00 AM | Extra-Practice | Bible Street Park | |
| Tuesday | October 27, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Thursday | October 29, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Friday | October 30, 2026 | 3:45 PM | 5:15 PM | Extra-Practice | Bible Street Park | |
| Sunday | November 1, 2026 | 1:30 PM | 3:00 PM | Game | Greenwich High School | vs. Generals |
| Tuesday | November 3, 2026 | 4:30 PM | 6:00 PM | Extra-Practice | Cos Cob School | |
| Thursday | November 5, 2026 | 4:30 PM | 6:00 PM | Extra-Practice | Cos Cob School | |
| Saturday | November 7, 2026 | 9:30 AM | 11:00 AM | Extra-Practice | Cos Cob School | |
| Sunday | November 8, 2026 | 1:30 PM | 3:00 PM | Game | Greenwich High School | vs. Generals |
| Tuesday | November 10, 2026 | 4:30 PM | 6:00 PM | Extra-Practice | Cos Cob School | |
| Thursday | November 12, 2026 | 4:30 PM | 6:00 PM | Extra-Practice | Cos Cob School | |
| Friday | November 13, 2026 | 4:30 PM | 6:00 PM | Extra-Practice | Cos Cob School | |
| Saturday | November 14, 2026 | 8:00 AM | 9:30 AM | Extra-Practice | Cos Cob School | |
| Sunday | November 15, 2026 | 1:30 PM | 3:00 PM | Game | Greenwich High School | vs. TBD Championship |
| Sunday | November 15, 2026 | 6:00 PM | 7:30 PM | Other | Greenwich High School | |
| Sunday | November 29, 2026 | 5:00 PM | 8:00 PM | Other | Hyatt Regency Greenwich |