| 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 7 | Pleasantville 6 | Non-league. High school. |
| Friday, September 13, 2019 | 6:30 PM | Port Jervis 34 | O'Neill 14 | Crossover. West Point Prep School. |
| Friday, September 20, 2019 | 7:00 PM | Rondout Valley 8 | Port Jervis 67 | League. Glennette Field. |
| Friday, September 27, 2019 | 7:00 PM | Minisink Valley 13 | Port Jervis 27 | Non-League. Glennette Field. |
| Saturday, October 5, 2019 | 1:30 PM | Port Jervis 34 | Red Hook 7 | League. High School. |
| Friday, October 11, 2019 | 7:00 PM | Middletown 57 | Port Jervis 14 | Non-League. Glennette Field. |
| Saturday, October 19, 2019 | 1:30 PM | Port Jervis 42 | Liberty 13 | Crossover. High School. |
| Friday, October 25, 2019 | 7:00 PM | Marlboro 28 | Port Jervis 20 | League. Glennette Field. |
| Saturday, November 2, 2019 | 3:00 PM | Port Jervis 14 | Burke Catholic 7 | Faller Field, Middletown. Class B semifinal. |
| Friday, November 8, 2019 | 7:00 PM | Port Jervis 27 | Marlboro 24 | Section 9 Class B final. Faller Field, Middletown. |
| Saturday, November 16, 2019 | 1:00 PM | Port Jervis 20 | Ardsley 14 | Mahopac High School. NYS Class B Regional Playoff. |
| Saturday, November 23, 2019 | 3:00 PM | Port Jervis | Schuylerville | NYS Class B semi-final. Faller Field, Middletown. |
| End of regular season |
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