| Date | Time | Visitor | Home | Comments |
| Saturday, August 31, 2019 | 9:00 AM | Port Jervis | Goshen | Scrimmage. Goshen, Burke, Middletown. |
| Saturday, September 7, 2019 | 1:30 PM | Port Jervis | Pleasantville | Non-league. High school. |
| Friday, September 13, 2019 | 6:30 PM | Port Jervis | O'Neill | Crossover. West Point Prep School. |
| Friday, September 20, 2019 | 7:00 PM | Rondout Valley | Port Jervis | League. Glennette Field. |
| Friday, September 27, 2019 | 7:00 PM | Minisink Valley | Port Jervis | Non-League. Glennette Field. |
| Saturday, October 5, 2019 | 1:30 PM | Port Jervis | Red Hook | League. High School. |
| Friday, October 11, 2019 | 7:00 PM | Middletown | Port Jervis | Non-League. Glennette Field. |
| Saturday, October 19, 2019 | 1:30 PM | Port Jervis | Liberty | Crossover. High School. |
| Friday, October 25, 2019 | 7:00 PM | Marlboro | Port Jervis | League. Glennette Field. |
| End of regular season |
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