| Date | Time | Visitor | Home | Comments |
| Friday, September 3, 2021 | 7:00 PM | Cornwall 36 | Port Jervis 0 | Non-league. Glennette Field. |
| Saturday, September 11, 2021 | 1:30 PM | Port Jervis 53 | Liberty 0 | League. Liberty High School. |
| Friday, September 17, 2021 | 7:00 PM | Port Jervis 35 | Minisink Valley 20 | Non-League. Minisink Valley HS. |
| Friday, September 24, 2021 | 7:00 PM | Marlboro 12 | Port Jervis 14 | League. Glennette Field. |
| Friday, October 1, 2021 | 7:00 PM | Middletown | Port Jervis | Non-League. Glennette Field. |
| Friday, October 8, 2021 | 7:00 PM | Burke Catholic | Port Jervis | League. Glennette Field. |
| Friday, October 15, 2021 | 7:00 PM | Red Hook | Port Jervis | League. Glennette Field. |
| Friday, October 22, 2021 | 6:30 PM | Port Jervis | New Paltz | League. New Paltz High School. |
| Friday, October 29, 2021 | 7:00 PM | Port Jervis | Rondout Valley | League. Rondout Central School. |
| End of regular season |
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