| 9/5/2019 | Southwestern Oklahoma State | 35 | at | Southeastern Oklahoma State (1-10,1-10) | 17 | | | |
| 9/14/2019 | East Central (3-8,3-8) | 21 | at | Southwestern Oklahoma State | 24 | | | |
| 9/21/2019 | Southwestern Oklahoma State | 9 | at | Arkansas-Monticello (5-6,5-6) | 44 | | | |
| 9/28/2019 | Ouachita (11-1,11-0) | 26 | at | Southwestern Oklahoma State | 21 | | | |
| 10/5/2019 | Southwestern Oklahoma State | 20 | at | Southern Arkansas (8-4,8-3) | 42 | | | |
| 10/12/2019 | Henderson State (9-3,9-2) | 35 | at | Southwestern Oklahoma State | 7 | | | |
| 10/19/2019 | Southwestern Oklahoma State | 14 | at | Harding (10-2,10-1) | 45 | | | |
| 10/26/2019 | Arkansas Tech (3-8,3-8) | 36 | at | Southwestern Oklahoma State | 35 | | | |
| 11/2/2019 | Southern Nazarene (2-9,2-9) | 7 | at | Southwestern Oklahoma State | 28 | | | |
| 11/9/2019 | Southwestern Oklahoma State | 21 | at | Oklahoma Baptist (7-4,7-4) | 35 | | | |
| 11/16/2019 | Southwestern Oklahoma State | 16 | at | Northwestern Oklahoma State (4-7,4-7) | 28 | | | |