| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Saturday | April 3, 2027 | 10:30 AM | 11:30 AM | Game | Fairfield University | @ Fairfield Prep |
| Wednesday | April 7, 2027 | 5:00 PM | 6:00 PM | Game | Darien High School | vs. Chaminade |
| Saturday | April 10, 2027 | 10:30 AM | 11:30 AM | Game | Manhasset Secondary School | @ Manhasset |
| Thursday | April 15, 2027 | 4:30 PM | 5:30 PM | Game | Ridgefield High School | @ Ridgefield |
| Friday | April 16, 2027 | 5:00 PM | 6:00 PM | Game | Darien High School | vs. St Anthony's |
| Tuesday | April 20, 2027 | 4:00 PM | 5:00 PM | Game | Darien High School | vs. Fairfield Ludlowe |
| Thursday | April 22, 2027 | 4:00 PM | 5:00 PM | Game | Wakeman Field | @ Staples |
| Saturday | April 24, 2027 | 10:30 AM | 11:30 AM | Game | Darien High School | vs. Yorktown |
| Tuesday | April 27, 2027 | 4:00 PM | 5:00 PM | Game | Darien High School | vs. Greenwich |
| Thursday | April 29, 2027 | 5:00 PM | 6:00 PM | Game | St. Anthony's High School | @ St Anthony's |
| Saturday | May 1, 2027 | 5:00 PM | 6:00 PM | Game | Darien High School | vs. New Canaan |
| Thursday | May 6, 2027 | 4:00 PM | 5:00 PM | Game | Darien High School | vs. Mamaroneck |
| Saturday | May 8, 2027 | 10:30 AM | 11:30 AM | Game | Darien High School | vs. Summit |
| Thursday | May 13, 2027 | 4:00 PM | 5:00 PM | Game | Darien High School | vs. Wilton |
| Saturday | May 15, 2027 | 10:30 AM | 11:30 AM | Game | Darien High School | vs. Massapequa |
| Tuesday | May 18, 2027 | 6:00 PM | 7:00 PM | Game | St. Joseph High School | @ St. Joseph's |