| THU 8/314:00 PM | Scrimmage | Boys Football Varsity
| | Darien High School
DHS Stadium Field
Trumbull: 2:45 PM - 2 Buses |
| FRI 9/87:00 PM | Non-League | Boys Football Varsity
| | North Haven Middle School
Vanacore Field
Darien: 2:30 PM - 3 buses needed |
| FRI 9/153:30 PM | | Boys Football Varsity
| | Darien High School
DHS Stadium Field
|
| FRI 9/226:00 PM | Non-League | Boys Football Varsity
| | Darien High School
DHS Stadium Field
|
| FRI 9/297:00 PM | | Boys Football Varsity
| | Norwalk High School
Testa Field
Darien: 4:30 PM - 2 buses needed |
| SAT 10/142:00 PM | | Boys Football Varsity
| | Greenwich High School
Cardinal Stadium
Darien: 11:00 AM - 3 buses needed |
| SAT 10/211:30 PM | | Boys Football Varsity
| | Darien High School
DHS Stadium Field
Fairfield Ludlowe: 11:45 AM - 2 Buses - Two buses |
| FRI 10/277:00 PM | | Boys Football Varsity
| | Darien High School
DHS Stadium Field
|
| FRI 11/37:00 PM | | Boys Football Varsity
| | Darien High School
DHS Stadium Field
Fairfield Warde: 5:00 PM - 2 Buses - One Cheer Bus; 5:30pm pick up, 9pm return |
| SAT 11/1111:00 AM | | Boys Football Varsity
Bridgeport Central - LL 6 | | Bridgeport Central
Kennedy Stadium Turf
Darien: 8:30 AM - 3 buses needed |
| THU 11/2310:00 AM | | Boys Football Varsity
| | New Canaan HS
Dunning Stadium
Darien: 7:30 AM - 3 buses needed |
| TUE 11/286:30 PM | | Boys Football Varsity
| | Naugatuck High School
Veterans Field
Darien: 2:30 PM - 3 buses |
| SUN 12/312:30 PM | | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
Darien: 9:15 AM - 3 buses |
| SAT 12/91:30 PM | | Boys Football Varsity
| | Rentschler Field
Rentschler Field
|