| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | September 24, 2025 | 7:00 PM | 8:00 PM | Meeting | Darien High School | |
| Monday | March 9, 2026 | 3:00 PM | 4:15 PM | Training | Chelsea Piers Connecticut | |
| Tuesday | March 10, 2026 | 3:00 PM | 4:15 PM | Training | Chelsea Piers Connecticut | |
| Wednesday | March 11, 2026 | 3:00 PM | 4:15 PM | Training | Chelsea Piers Connecticut | |
| Thursday | March 12, 2026 | 3:00 PM | 4:15 PM | Training | Chelsea Piers Connecticut | |
| Friday | March 13, 2026 | 3:00 PM | 4:15 PM | Training | Darien High School | |
| Monday | March 16, 2026 | 2:45 PM | 4:45 PM | Training | Darien High School | |
| Tuesday | March 17, 2026 | 2:45 PM | 4:45 PM | Training | Darien High School | |
| Wednesday | March 18, 2026 | 2:45 PM | 4:45 PM | Training | Darien High School | |
| Thursday | March 19, 2026 | 2:45 PM | 4:45 PM | Training | Darien High School | |
| Friday | March 20, 2026 | 2:45 PM | 3:45 PM | Training | Darien High School | |
| Saturday | March 21, 2026 | 8:00 AM | 11:00 AM | Extra-Practice | Darien High School | |
| Monday | March 23, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Tuesday | March 24, 2026 | 3:00 PM | 4:30 PM | Game | Darien High School | vs. JV v Freshmen Scrimmage |
| Wednesday | March 25, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Thursday | March 26, 2026 | 4:30 PM | 6:00 PM | Game | Darien High School | vs. Iona Prep Scrimmaage |
| Friday | March 27, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Saturday | March 28, 2026 | TBD | TBD | Game | Darien High School | vs. Jamboree Scrimmage |
| Monday | March 30, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Tuesday | March 31, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Wednesday | April 1, 2026 | 3:00 PM | 4:30 PM | Game | Darien High School | vs. Blue V White Scrimmage |
| Thursday | April 2, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Friday | April 3, 2026 | 11:00 AM | 1:00 PM | Extra-Practice | Darien High School | |
| Saturday | April 4, 2026 | 10:30 AM | 12:00 PM | Game | Darien High School | vs. Fairfield Prep |
| Monday | April 6, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Tuesday | April 7, 2026 | 5:30 PM | 7:00 PM | Game | Fairfield Warde High School | @ Fairfield Warde |
| Wednesday | April 8, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Thursday | April 9, 2026 | 4:30 PM | 6:00 PM | Game | Yorktown Highschool | @ Yorktown |
| Friday | April 10, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Saturday | April 11, 2026 | 5:30 PM | 7:00 PM | Game | Darien High School | vs. Manhasset |
| Monday | April 13, 2026 | 1:00 PM | 3:00 PM | Extra-Practice | Darien High School | |
| Tuesday | April 14, 2026 | 5:30 PM | 7:00 PM | Game | Trumbull High School | @ Trumbull |
| Wednesday | April 15, 2026 | 1:00 PM | 3:00 PM | Extra-Practice | Darien High School | |
| Thursday | April 16, 2026 | 4:30 PM | 6:00 PM | Game | Wilton High School | @ Wilton |
| Friday | April 17, 2026 | 11:00 AM | 1:00 PM | Extra-Practice | Darien High School | |
| Saturday | April 18, 2026 | 10:30 AM | 12:00 PM | Game | Mamaroneck High School | @ Mamaroneck |
| Monday | April 20, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Tuesday | April 21, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Wednesday | April 22, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Thursday | April 23, 2026 | 4:00 PM | 5:30 PM | Game | Greenwich High School | @ Greenwich |
| Friday | April 24, 2026 | 2:45 PM | 3:45 PM | Extra-Practice | Darien High School | |
| Saturday | April 25, 2026 | 10:30 AM | 12:00 PM | Game | Darien High School | vs. Brunswick |
| Monday | April 27, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Tuesday | April 28, 2026 | 5:45 PM | 7:15 PM | Game | Darien High School | vs. Westhill |
| Wednesday | April 29, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Thursday | April 30, 2026 | 5:00 PM | 6:30 PM | Game | Darien High School | vs. St Anthony's |
| Friday | May 1, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Saturday | May 2, 2026 | TBD | TBD | Game | New Canaan High School | @ New Canaan |
| Monday | May 4, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Tuesday | May 5, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Wednesday | May 6, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Thursday | May 7, 2026 | 4:00 PM | 5:30 PM | Game | Darien High School | vs. Staples |
| Friday | May 8, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Saturday | May 9, 2026 | 10:30 AM | 12:00 PM | Game | Chaminade High School | @ Chaminade |
| Monday | May 11, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Tuesday | May 12, 2026 | 5:00 PM | 6:30 PM | Game | Massapequa High School (MHS) - Main Campus | @ Massapequa |
| Wednesday | May 13, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Thursday | May 14, 2026 | 2:45 PM | 5:15 PM | Extra-Practice | Darien High School | |
| Friday | May 15, 2026 | 2:45 PM | 4:45 PM | Extra-Practice | Darien High School | |
| Sunday | May 17, 2026 | 3:00 PM | 4:00 PM | Extra-Practice | Darien High School | |
| Monday | May 18, 2026 | 2:45 PM | 3:45 PM | Extra-Practice | Darien High School | |
| Tuesday | May 19, 2026 | 4:00 PM | 5:00 PM | Game | Darien High School | vs. Ridgefield |