| 8/29/2019 | Pikeville | 20 | at | Murray State (4-8) | 59 | | | at OVC |
| 9/7/2019 | Pikeville | 17 | at | Reinhardt (8-3,8-1) | 20 | OT | | |
| 9/14/2019 | Bluefield (3-8,3-7) | 6 | at | Pikeville | 48 | | | |
| 9/21/2019 | Kentucky Christian (3-8,3-7) | 38 | at | Pikeville | 49 | | | |
| 10/5/2019 | Cumberlands KY (10-2,10-1) | 24 | at | Pikeville | 13 | | | |
| 10/12/2019 | Pikeville | 37 | at | Georgetown KY (5-5,5-5) | 31 | | | |
| 10/19/2019 | Pikeville | 35 | at | Campbellsville (1-9,1-9) | 15 | | | |
| 10/26/2019 | Lindsey Wilson (12-1,10-0) | 45 | at | Pikeville | 10 | | | |
| 11/2/2019 | Pikeville | 27 | at | Cumberland TN (5-5,5-5) | 0 | | | |
| 11/9/2019 | Bethel TN (5-6,5-5) | 34 | at | Pikeville | 44 | | | |
| 11/16/2019 | Pikeville | 21 | at | Thomas More (4-7,4-6) | 34 | | | |