| 8/29/2019 | Dakota Wesleyan | 30 | at | Dakota State | 33 | 2OT | @ NSAA | |
| Ottawa AZ | 48 | at | Doane | 7 | Soon | |||
| Keiser | 34 | at | Dordt | 21 | MSC | |||
| Jamestown | 14 | at | Valley City State | 20 | @ NSAA | |||
| 8/31/2019 | Panhandle State | 22 | at | Hastings | 40 | Soon | ||
| St Francis IL | 0 | at | Morningside | 80 | MSFA | |||
| Midland U. | 48 | at | Southwestern | 17 | @ KCAC | |||
| Briar Cliff | 10 | at | Waldorf | 17 | @ NSAA | |||
| 9/7/2019 | Dakota State | 10 | at | Briar Cliff | 13 | NSAA | ||
| Doane | 17 | at | Concordia NE | 10 | ||||
| Presentation | 0 | at | Dakota Wesleyan | 44 | NSAA | |||
| Waldorf | 9 | at | Dordt | 30 | NSAA | |||
| Dickinson State | 34 | at | Jamestown | 0 | NSAA | |||
| Valley City State | 7 | at | Northwestern IA | 47 | NSAA | |||
| 9/14/2019 | Dakota Wesleyan | 0 | at | Briar Cliff | 47 | |||
| Concordia NE | 24 | at | Buena Vista | 27 | @ ARC (D3) | |||
| Jamestown | 21 | at | Hastings | 38 | ||||
| Northwestern IA | 26 | at | Midland U. | 25 | ||||
| Dordt | 14 | at | Morningside | 56 | ||||
| Doane | 3 | at | Tarleton State | 56 | @ LSC (D2) | |||
| 9/21/2019 | Doane | 10 | at | Briar Cliff | 20 | |||
| Northwestern IA | 52 | at | Dakota Wesleyan | 7 | ||||
| Concordia NE | 44 | at | Hastings | 0 | ||||
| Dordt | 41 | at | Jamestown | 16 | ||||
| Midland U. | 29 | at | Morningside | 51 | ||||
| 9/28/2019 | Briar Cliff | 14 | at | Concordia NE | 16 | |||
| Hastings | 12 | at | Doane | 37 | ||||
| Dakota Wesleyan | 22 | at | Dordt | 57 | ||||
| Missouri Baptist | 47 | at | Midland U. | 44 | MSFA | |||
| Jamestown | 6 | at | Northwestern IA | 45 | ||||
| 10/5/2019 | Doane | 38 | at | Dakota Wesleyan | 20 | |||
| Morningside | 69 | at | Hastings | 13 | ||||
| Concordia NE | 10 | at | Jamestown | 13 | 4OT | |||
| Briar Cliff | 13 | at | Midland U. | 7 | ||||
| 10/12/2019 | Morningside | 49 | at | Briar Cliff | 14 | |||
| Dakota Wesleyan | 17 | at | Concordia NE | 24 | ||||
| Jamestown | 21 | at | Doane | 28 | ||||
| Northwestern IA | 35 | at | Dordt | 6 | ||||
| Midland U. | 61 | at | Hastings | 20 | ||||
| 10/19/2019 | Northwestern IA | 20 | at | Concordia NE | 14 | |||
| Dordt | 61 | at | Doane | 0 | ||||
| Dakota Wesleyan | 27 | at | Midland U. | 52 | ||||
| Jamestown | 0 | at | Morningside | 61 | ||||
| 10/26/2019 | Hastings | 0 | at | Briar Cliff | 32 | |||
| Morningside | 69 | at | Dakota Wesleyan | 0 | ||||
| Concordia NE | 0 | at | Dordt | 35 | ||||
| Midland U. | 42 | at | Jamestown | 14 | ||||
| Doane | 3 | at | Northwestern IA | 23 | ||||
| 11/2/2019 | Northwestern IA | 38 | at | Briar Cliff | 7 | |||
| Midland U. | 27 | at | Concordia NE | 7 | ||||
| Morningside | 42 | at | Doane | 10 | ||||
| Dordt | 70 | at | Hastings | 28 | ||||
| 11/9/2019 | Jamestown | 14 | at | Dakota Wesleyan | 41 | |||
| Briar Cliff | 7 | at | Dordt | 43 | ||||
| Doane | 7 | at | Midland U. | 31 | ||||
| Concordia NE | 7 | at | Morningside | 52 | ||||
| Hastings | 17 | at | Northwestern IA | 44 | ||||
| 11/16/2019 | Hastings | 7 | at | Dakota Wesleyan | 30 | |||
| Midland U. | 31 | at | Dordt | 28 | ||||
| Briar Cliff | 10 | at | Jamestown | 31 | ||||
| Morningside | 37 | at | Northwestern IA | 27 | ||||
| 11/23/2019 | Dickinson State | 14 | at | Morningside | 57 | NAIA Playoffs | NSAA | |
| St Xavier | 25 | at | Northwestern IA | 20 | NAIA Playoffs | MSFA | ||
| 11/30/2019 | St Xavier | 0 | at | Morningside | 51 | NAIA Quarterfinals | MSFA | |
| 12/7/2019 | Grand View | 16 | at | Morningside | 21 | NAIA Semifinal | HAAC | |
| 12/21/2019 | Marian IN | 38 | vs | Morningside | 40 | NAIA Championship - Grambling LA | vs MSFA |