| Date | Opponent(s) | Result | Caption | Location | Transportation | ||
|---|---|---|---|---|---|---|---|
| Sat9/5/26 |
Pawling Multi-scrimmage 
|
10:00 AM ET | Scrimmage | Pawling High School | |||
| Thu9/10/26 |
vs
Rockland Central
|
PPD | Postponed to 9/14/26 | Stissing Mountain Pine Plains High School | |||
| Mon9/14/26 |
vs
Rockland Central
|
W 48-0 | Postponed from 9/10/26 | Stissing Mountain Pine Plains High School | |||
| Fri9/18/26 |
@
Fallsburg
|
W 34-8 | Morningside Park | ||||
| Fri9/25/26 |
vs
Ellenville
|
L 30-44 | C | Stissing Mountain Pine Plains High School | |||
| Fri10/2/26 |
vs
Pawling
|
L 20-62 | C | Stissing Mountain Pine Plains High School | |||
| Thu10/8/26 |
vs
Tri Valley
|
L 32-46 | Stissing Mountain Pine Plains High School | ||||
| Thu10/15/26 |
@
Millbrook / Webutuck
|
L 6-16 | C | Millbrook High School | |||
| Fri10/23/26 |
vs
Onteora
|
W 34-32 | C | Stissing Mountain Pine Plains High School | |||
| Thu10/29/26 |
@
Rockland Central
|
CXL | Cancelled | Rockland Middle/High School HS/MS Football Field | |||
| Fri10/30/26 |
@
Corinth Central
|
L 14-51 | Corinth Central High School |