| THU 8/244:00 PM | Scrimmage | Boys Football Freshman
| | Newtown High School
Blue and Gold Stadium
Bethel: 2:30 PM - 1 Bus |
| THU 8/314:00 PM | Scrimmage | Boys Football Freshman
Newtown - L Fairfield Warde - L | | Newtown High School
Back Turf Field
Fairfield Warde: 2:30 PM |
| THU 8/316:00 PM | Scrimmage | Boys Football Varsity
Newtown - L Fairfield Warde - L | | Newtown High School
Blue and Gold Stadium
Fairfield Warde: 4:00 PM - 2 Buses |
| SAT 9/910:00 AM | Non-League | Boys Football Freshman
Newtown - L St. Joseph - M | | Newtown High School
NHS Back Turf Field
St. Joseph: 12:01 AM |
| SAT 9/97:00 PM | Non-League | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
|
| MON 9/114:00 PM | Non-League | Boys Football Junior Varsity
St. Joseph - M Newtown - L | | St. Joseph High School
Upper Turf
Newtown: 2:45 PM - 1 Bus |
| THU 9/144:00 PM | | Boys Football Freshman
New Milford - L Newtown - L | | New Milford High School
North Turf Field - NMHS
Newtown: 2:45 PM - 1 Bus |
| FRI 9/154:00 PM | Non-League | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
New Milford: 2:15 PM |
| SUN 9/179:00 AM | | Boys Football Other
| | Shelton High School
Finn Stadium
|
| MON 9/183:45 PM | | Boys Football Junior Varsity
New Milford - L Newtown - L | | New Milford High School
North Turf Field - NMHS
Newtown: 8:45 AM - 1 Bus |
| THU 9/214:00 PM | Non-League | Boys Football Freshman
Newtown - L Trumbull - LL | | Treadwell Park
Newtown Treadwell Park
Trumbull: 2:45 PM - 1 Bus |
| FRI 9/227:00 PM | Non-League | Boys Football Varsity
| | Trumbull High School
McDougall Stadium
Newtown: 4:45 PM - 1 Bus |
| SAT 9/2310:30 AM | | Boys Football Junior Varsity
Trumbull - LL Newtown - L | | Trumbull High School
McDougall Stadium
Newtown: 9:00 AM - 1 Bus |
| THU 9/284:30 PM | | Boys Football Freshman
Newtown - L Stratford - MM | | Newtown High School
NHS Back Turf Field
Stratford: 2:45 PM - 1 Bus |
| FRI 9/297:00 PM | | Boys Football Varsity
| | Penders Field
Penders Field - Stratford
Newtown: 4:15 PM - 2 Buses |
| SAT 9/309:00 AM | | Boys Football Junior Varsity
Newtown - L Stratford - MM | | Newtown High School
NHS Back Turf Field
Stratford: 7:15 AM - 1 Bus |
| THU 10/125:00 PM | Non-League | Boys Football Freshman
Newtown - L Daniel Hand - M | | Newtown High School
NHS Back Turf Field
Daniel Hand: 3:00 PM - 1 Bus |
| FRI 10/137:00 PM | | Boys Football Varsity
| | New Fairfield High School
Stadium Field
Newtown: 4:30 PM - 1 Bus |
| SAT 10/149:30 AM | | Boys Football Junior Varsity
Newtown - L Fairfield Ludlowe - L | | Newtown High School
NHS Back Turf Field
Fairfield Ludlowe: 7:45 AM |
| THU 10/194:30 PM | Non-League | Boys Football Freshman
| | Newtown High School
NHS Back Turf Field
Sheehan: 2:45 PM |
| FRI 10/207:00 PM | Non-League | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
Weston: 3:30 PM |
| SAT 10/2110:00 AM | | Boys Football Junior Varsity
| | Staples High School
Staples Stadium
|
| THU 10/266:00 PM | | Boys Football Freshman
West Haven - LL Newtown - L | | West Haven High School
Ken Strong Stadium
Newtown: 4:00 PM - 1 Bus |
| FRI 10/277:00 PM | Non-League | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
|
| SAT 10/2810:30 AM | | Boys Football Junior Varsity
West Haven - LL Newtown - L | | West Haven High School
Ken Strong Stadium
Newtown: 8:30 AM - 1 Bus |
| THU 11/24:00 PM | | Boys Football Freshman
Newtown - L Pomperaug - MM | | Newtown High School
NHS Back Turf Field
Pomperaug: 2:30 PM |
| FRI 11/36:30 PM | | Boys Football Varsity
| | Pomperaug High School
Stadium
Newtown: 4:30 PM - 1 Bus |
| SAT 11/49:00 AM | | Boys Football Junior Varsity
Newtown - L Pomperaug - MM | | Newtown High School
Blue and Gold Stadium
Pomperaug: 7:45 AM |
| WED 11/86:00 PM | | Boys Football Freshman
Newtown - L Jonathan Law - SS | | Newtown High School
Blue and Gold Stadium
Jonathan Law: 4:00 PM - 1 Bus |
| FRI 11/107:00 PM | | Boys Football Varsity
| | Bunnell HS
Mastroni Field
Newtown: 4:30 PM - 1 Bus |
| SAT 11/1110:00 AM | | Boys Football Junior Varsity
| | Newtown High School
Blue and Gold Stadium
Bunnell: 8:00 AM - 1 Bus |
| THU 11/166:00 PM | | Boys Football Freshman
| | Masuk High School
Benedict Stadium Field @ Masuk HS
Newtown: 5:00 PM - 1 Bus |
| SAT 11/1810:00 AM | | Boys Football Junior Varsity
| | Masuk High School
Benedict Stadium Field @ Masuk HS
Newtown: 8:45 AM - 1 Bus |
| WED 11/226:00 PM | Non-League | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
Masuk: 4:45 PM - 2 Buses |
| TUE 11/286:30 PM | Postseason | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
|
| SUN 12/312:30 PM | | Boys Football Varsity
| | Newtown High School
Blue and Gold Stadium
Darien: 9:15 AM - 3 buses |