| 8/29/2019 | Jamestown | 14 | at | Valley City State (7-3) | 20 | at NSAA | ||
| 9/7/2019 | Dickinson State (8-3) | 34 | at | Jamestown | 0 | NSAA | ||
| 9/14/2019 | Jamestown | 21 | at | Hastings (2-8,1-8) | 38 | |||
| 9/21/2019 | Dordt (7-4,6-3) | 41 | at | Jamestown | 16 | |||
| 9/28/2019 | Jamestown | 6 | at | Northwestern IA (9-2,8-1) | 45 | |||
| 10/5/2019 | Concordia NE (3-7,3-6) | 10 | at | Jamestown | 13 | 4OT | ||
| 10/12/2019 | Jamestown | 21 | at | Doane (4-7,4-5) | 28 | |||
| 10/19/2019 | Jamestown | 0 | at | Morningside (14-0,9-0) | 61 | |||
| 10/26/2019 | Midland U. (7-4,6-3) | 42 | at | Jamestown | 14 | |||
| 11/9/2019 | Jamestown | 14 | at | Dakota Wesleyan (3-8,2-7) | 41 | |||
| 11/16/2019 | Briar Cliff (5-6,4-5) | 10 | at | Jamestown | 31 |
| vs Jamestown | vs Other Opponents | Jamestown compared to OOs | |
| Record: | 9-2 | 60-50 | |
| Points Scored: | 33.64 | 28.13 | -5.51 |
| Points Allowed: | 13.64 | 24.79 | -11.15 |
| Margin: | 20.00 | 3.34 | -16.66 |
| Total Points: | 47.28 | 52.92 | -5.64 |