| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Thursday | March 25, 2027 | 5:00 PM | 6:30 PM | Game | Darien High School | vs. Iona Prep Scrimmage |
| Sunday | March 28, 2027 | 9:00 AM | 1:00 PM | Game | Darien High School | vs. Jamboree |
| Saturday | April 3, 2027 | 1:00 PM | 2:30 PM | Game | Fairfield University | @ Fairfield Prep |
| Wednesday | April 7, 2027 | 6:00 PM | 7:30 PM | Game | Darien High School | vs. Chaminade |
| Saturday | April 10, 2027 | 1:00 PM | 2:30 PM | Game | Manhasset Secondary School | @ Manhassett |
| Thursday | April 15, 2027 | 6:30 PM | 8:00 PM | Game | Ridgefield High School | @ Ridgefield |
| Saturday | April 17, 2027 | 2:30 PM | 4:00 PM | Game | Stadium at Rustin High School | @ Springfield Pa |
| Tuesday | April 20, 2027 | 6:00 PM | 7:30 PM | Game | Darien High School | vs. Fairfield Ludlowe |
| Thursday | April 22, 2027 | 6:30 PM | 8:00 PM | Game | Staples High School | @ Staples |
| Saturday | April 24, 2027 | 1:00 PM | 2:30 PM | Game | Darien High School | vs. Yorktown |
| Tuesday | April 27, 2027 | 6:00 PM | 7:30 PM | Game | Darien High School | vs. Greenwich |
| Thursday | April 29, 2027 | 7:00 PM | 8:30 PM | Game | St. Anthony's High School | @ St Anthony's |
| Saturday | May 1, 2027 | 3:30 PM | 5:00 PM | Game | Darien High School | vs. New Canaan |
| Thursday | May 6, 2027 | 6:00 PM | 7:30 PM | Game | Darien High School | vs. Mamaroneck |
| Saturday | May 8, 2027 | 1:00 PM | 2:00 PM | Game | Darien High School | vs. Summit |
| Thursday | May 13, 2027 | 6:00 PM | 7:30 PM | Game | Darien High School | vs. Wilton |
| Saturday | May 15, 2027 | 1:00 PM | 2:30 PM | Game | Darien High School | vs. Massapequa |
| Tuesday | May 18, 2027 | 4:30 PM | 6:00 PM | Game | St. Joseph High School | @ St. Joseph's |
| Friday | May 21, 2027 | TBD | TBD | Game | Darien High School | @ FCIAC 1/4 Finals |
| Tuesday | May 25, 2027 | TBD | TBD | Game | Wilton High School | @ FCIAC SEMI FINALS - TBD |
| Thursday | May 27, 2027 | 6:30 PM | 8:00 PM | Game | Wilton High School | @ FCIAC FINALS - TBD |
| Wednesday | June 2, 2027 | 4:00 PM | 5:30 PM | Game | Darien High School | vs. STATE CLASS LL PLAYOFFS - TBD |
| Saturday | June 5, 2027 | 3:00 PM | 4:30 PM | Game | Darien High School | vs. STATE CLASS LL 1/4 FINALS - TBD |
| Wednesday | June 9, 2027 | TBD | TBD | Game | Fairfield University | @ STATE CLASS LL SEMI FINALS - TBD |
| Saturday | June 12, 2027 | TBD | TBD | Game | Fairfield University | @ STATE CLASS LL FINALS |