Stadium: Georgetown Stadium Comple Round: 1
| 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 |
| NCAAF | 2019/09/07 18:00 | Sewanee Tigers v Southwestern Pirates | W | 7-47 |
| NCAAF | 2019/11/02 21:00 | Howard Payne Yellow Jackets v Sul Ross State Lobos | W | 31-20 |
| NCAAF | 2019/10/26 19:00 | East Texas Baptist Tigers v Howard Payne Yellow Jackets | L | 41-35 |
| NCAAF | 2019/10/19 18:00 | Howard Payne Yellow Jackets v Texas Lutheran Bulldogs | L | 14-27 |
| NCAAF | 2019/10/05 18:00 | Howard Payne Yellow Jackets v Louisiana College Wildcats | L | 21-27 |
| NCAAF | 2019/09/28 23:00 | Mary Hardin Baylor v Howard Payne Yellow Jackets | L | 65-0 |
| NCAAF | 2019/09/21 18:00 | Howard Payne Yellow Jackets v Hardin Simmons Cowboys | L | 20-63 |
| NCAAF | 2019/09/14 18:00 | Mcmurry Warhawks v Howard Payne Yellow Jackets | W | 37-56 |
| NCAAF | 2019/09/07 18:00 | Austin Kangaroos v Howard Payne Yellow Jackets | W | 34-48 |