Stadium: Bob Shelton Stadium Round: 1
| NCAAF | 2019/11/09 20:00 | East Texas Baptist Tigers v Hardin Simmons Cowboys | W | 0-45 |
| NCAAF | 2019/11/02 18:00 | Hardin Simmons Cowboys v Mcmurry Warhawks | W | 91-29 |
| NCAAF | 2019/10/26 18:00 | Mary Hardin Baylor v Hardin Simmons Cowboys | L | 15-14 |
| NCAAF | 2019/10/19 18:00 | Hardin Simmons Cowboys v Belhaven Blazers | W | 63-7 |
| NCAAF | 2019/10/05 23:00 | Hardin Simmons Cowboys v Texas Lutheran Bulldogs | L | 27-38 |
| NCAAF | 2019/09/28 17:00 | Louisiana College Wildcats v Hardin Simmons Cowboys | W | 6-51 |
| NCAAF | 2019/09/21 18:00 | Howard Payne Yellow Jackets v Hardin Simmons Cowboys | W | 20-63 |
| NCAAF | 2019/09/14 23:00 | Hardin Simmons Cowboys v Trinity Tigers | W | 16-10 |
| NCAAF | 2019/11/09 19:00 | Southwestern Pirates v Howard Payne Yellow Jackets | L | 16-24 |
| NCAAF | 2019/11/02 18:00 | Southwestern Pirates v East Texas Baptist Tigers | L | 23-49 |
| NCAAF | 2019/10/26 18:00 | Mcmurry Warhawks v Southwestern Pirates | W | 25-29 |
| NCAAF | 2019/10/19 18:00 | Southwestern Pirates v Mary Hardin Baylor | L | 3-33 |
| NCAAF | 2019/10/12 18:00 | Belhaven Blazers v Southwestern Pirates | W | 21-31 |
| NCAAF | 2019/10/05 18:00 | Southwestern Pirates v Sul Ross State Lobos | L | 9-21 |
| NCAAF | 2019/09/28 23:00 | Texas Lutheran Bulldogs v Southwestern Pirates | L | 27-0 |
| NCAAF | 2019/09/21 23:00 | Southwestern Pirates v Louisiana College Wildcats | W | 50-3 |