Stadium: Milam Stadium Round: 1
| NCAAF | 2022/09/02 00:00 | Henderson State Reddies v Southwestern Oklahoma State Bulldogs | L | 30-13 |
| NCAAF | 2021/09/02 23:00 | Southwestern Oklahoma State Bulldogs v Henderson State Reddies | L | 13-31 |
| NCAAF | 2019/10/12 19:00 | Southwestern Oklahoma State Bulldogs v Henderson State Reddies | L | 7-35 |
| NCAAF | 2018/09/22 23:00 | Henderson State Reddies v Southwestern Oklahoma State Bulldogs | W | 31-35 |
| NCAAF | 2023/10/28 19:00 | Southern Arkansas Muleriders v Southwestern Oklahoma State Bulldogs | L | 41-10 |
| NCAAF | 2023/10/21 19:00 | Southeastern Oklahoma State Savage Storm v Southwestern Oklahoma State Bulldogs | L | 32-13 |
| NCAAF | 2023/10/14 19:00 | Southwestern Oklahoma State Bulldogs v Oklahoma Baptist Bison | L | 13-20 |
| NCAAF | 2023/10/07 22:30 | Southwestern Oklahoma State Bulldogs v Arkansas Tech Wonder Boys | L | 7-9 |
| NCAAF | 2023/09/30 23:00 | Harding Bisons v Southwestern Oklahoma State Bulldogs | L | 64-0 |
| NCAAF | 2023/09/23 19:00 | Southern Nazarene v Southwestern Oklahoma State Bulldogs | L | 41-7 |
| NCAAF | 2023/09/16 23:00 | Southwestern Oklahoma State Bulldogs v East Central Tigers | L | 13-24 |
| NCAAF | 2023/09/09 23:00 | Arkansas Monticello Boll Weevils v Southwestern Oklahoma State Bulldogs | L | 58-21 |
| NCAAF | 2023/10/28 19:00 | Henderson State Reddies v Northwestern Oklahoma State Rangers | W | 51-0 |
| NCAAF | 2023/10/21 19:00 | Arkansas Monticello Boll Weevils v Henderson State Reddies | W | 14-42 |
| NCAAF | 2023/10/14 19:00 | Henderson State Reddies v Southern Arkansas Muleriders | L | 34-35 |
| NCAAF | 2023/10/07 19:00 | Henderson State Reddies v Southern Nazarene | W | 42-28 |
| NCAAF | 2023/10/01 00:00 | Oklahoma Baptist Bison v Henderson State Reddies | W | 14-27 |
| NCAAF | 2023/09/23 23:00 | Henderson State Reddies v Harding Bisons | L | 16-27 |
| NCAAF | 2023/09/16 23:00 | Arkansas Tech Wonder Boys v Henderson State Reddies | W | 24-27 |
| NCAAF | 2023/09/09 23:00 | Southeastern Oklahoma State Savage Storm v Henderson State Reddies | W | 28-38 |