| SAT 9/9Canceled | Non-League | Boys Football Junior Varsity
Darien - L North Haven - MM | | Darien High School
DHS Stadium East
North Haven: 7:45 AM |
| MON 9/185:30 PM | | Boys Football Junior Varsity
Brien McMahon - LL Darien - L | | Brien McMahon High School
Casagrande Field
Darien: 4:15 PM |
| SAT 9/2310:00 AM | | Boys Football Junior Varsity
Fairfield Prep - LL Darien - L | | Fairfield University
Barlow Field
Darien: 8:00 AM |
| SAT 9/302:30 PM | | Boys Football Junior Varsity
| | Norwalk High School
Testa Field
Darien: 1:00 PM |
| MON 10/164:00 PM | | Boys Football Junior Varsity
Darien - L Greenwich - LL | | Darien High School
DHS Stadium East
Greenwich: 2:45 PM - 1 Bus |
| MON 10/234:30 PM | | Boys Football Junior Varsity
Fairfield Ludlowe - L Darien - L | | Tomlinson MS
Turf Field
Darien: 2:30 PM |
| SAT 10/284:00 PM | | Boys Football Junior Varsity
| | Darien High School
DHS Stadium Field
|
| MON 11/64:30 PM | | Boys Football Junior Varsity
Fairfield Warde - L Darien - L | | Fairfield Warde High School
Tetreau/Davis Field
Darien: 2:30 PM |
| MON 11/134:00 PM | Non-League | Boys Football Junior Varsity
Darien - L Iona Preparatory School | | Darien High School
DHS Stadium Field
|
| FRI 11/174:30 PM | | Boys Football Junior Varsity
Darien - L New Canaan - L | | Darien High School
DHS Stadium Field
New Canaan: 2:30 PM - 1 Bus |