| 9/7/2019 | Cumberlands KY | 30 | at | Ave Maria (5-5,5-4) | 23 | OT | ||
| 9/19/2019 | Webber International (3-6,3-6) | 14 | at | Cumberlands KY | 45 | |||
| 9/28/2019 | Union KY (0-11,0-10) | 0 | at | Cumberlands KY | 98 | |||
| 10/5/2019 | Cumberlands KY | 24 | at | Pikeville (6-5,6-4) | 13 | |||
| 10/12/2019 | Bethel TN (5-6,5-5) | 21 | at | Cumberlands KY | 49 | |||
| 10/19/2019 | Cumberlands KY | 26 | at | Cumberland TN (5-5,5-5) | 8 | |||
| 10/26/2019 | Campbellsville (1-9,1-9) | 10 | at | Cumberlands KY | 47 | |||
| 11/2/2019 | Cumberlands KY | 14 | at | Georgetown KY (5-5,5-5) | 7 | |||
| 11/9/2019 | Cumberlands KY | 45 | at | Thomas More (4-7,4-6) | 31 | |||
| 11/16/2019 | Lindsey Wilson (12-1,10-0) | 24 | at | Cumberlands KY | 21 | |||
| 11/23/2019 | Cumberlands KY | 28 | at | Keiser (9-1,8-1) | 24 | NAIA Playoffs | ||
| 11/30/2019 | Cumberlands KY | 0 | at | Marian IN (12-1) | 30 | NAIA Quarterfinals | at MSFA |
| vs Cumberlands KY | vs Other Opponents | Cumberlands KY compared to OOs | |
| Record: | 2-10 | 65-52 | |
| Points Scored: | 17.08 | 28.10 | 11.02 |
| Points Allowed: | 35.58 | 26.79 | 8.79 |
| Margin: | -18.50 | 1.31 | 19.81 |
| Total Points: | 52.66 | 54.89 | -2.23 |