Stadium: Milam Stadium Round: 1
| 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 | 2019/11/16 21:00 | Northwestern Oklahoma State Rangers v Southwestern Oklahoma State Bulldogs | L | 28-16 |
| NCAAF | 2019/11/09 19:00 | Oklahoma Baptist Bison v Southwestern Oklahoma State Bulldogs | L | 35-21 |
| NCAAF | 2019/11/02 19:00 | Southwestern Oklahoma State Bulldogs v Southern Nazarene | W | 28-7 |
| NCAAF | 2019/10/26 22:30 | Southwestern Oklahoma State Bulldogs v Arkansas Tech Wonder Boys | L | 35-36 |
| NCAAF | 2019/10/19 20:00 | Harding Bisons v Southwestern Oklahoma State Bulldogs | L | 45-14 |
| NCAAF | 2019/10/12 19:00 | Southwestern Oklahoma State Bulldogs v Henderson State Reddies | L | 7-35 |
| NCAAF | 2019/10/05 19:00 | Southern Arkansas Muleriders v Southwestern Oklahoma State Bulldogs | L | 42-20 |
| NCAAF | 2019/09/28 19:00 | Southwestern Oklahoma State Bulldogs v Ouachita Baptist Tigers | L | 21-26 |
| NCAAF | 2019/11/16 19:00 | Ouachita Baptist Tigers v Henderson State Reddies | L | 24-21 |
| NCAAF | 2019/11/09 20:00 | Henderson State Reddies v Southern Arkansas Muleriders | W | 38-31 |
| NCAAF | 2019/11/02 20:00 | Arkansas Monticello Boll Weevils v Henderson State Reddies | W | 20-27 |
| NCAAF | 2019/10/26 19:00 | Southeastern Oklahoma State Savage Storm v Henderson State Reddies | W | 27-41 |
| NCAAF | 2019/10/19 19:00 | Henderson State Reddies v East Central Tigers | W | 48-17 |
| NCAAF | 2019/10/12 19:00 | Southwestern Oklahoma State Bulldogs v Henderson State Reddies | W | 7-35 |
| NCAAF | 2019/10/05 19:00 | Henderson State Reddies v Northwestern Oklahoma State Rangers | W | 47-7 |
| NCAAF | 2019/09/28 23:00 | Harding Bisons v Henderson State Reddies | L | 14-13 |