| 9/6/2019 | Hope | 21 | at | Millikin | 27 | MIAA | ||
| 9/7/2019 | North Park | 21 | at | Anderson | 34 | @ HCA | ||
| Coe | 3 | at | Augustana IL | 41 | ARC | |||
| Washington U | 43 | at | Chicago | 7 | @ MidW | |||
| North Central | 43 | at | Christopher Newport | 13 | @ NJAC | |||
| Carroll WI | 44 | at | Lakeland | 34 | @ NAC | |||
| Wheaton | 38 | at | Monmouth IL | 0 | @ MidW | |||
| Carthage | 19 | at | Wisconsin-Oshkosh | 20 | @ WIAC | |||
| 9/14/2019 | Aurora | 48 | at | Elmhurst | 22 | NAC | ||
| Illinois Wesleyan | 27 | at | Wisconsin-La Crosse | 33 | 2OT | @ WIAC | ||
| 9/21/2019 | Elmhurst | 13 | at | Augustana IL | 55 | |||
| Carroll WI | 7 | at | Carthage | 36 | ||||
| Millikin | 41 | at | North Park | 7 | ||||
| North Central | 46 | at | Washington U | 13 | ||||
| Illinois Wesleyan | 10 | at | Wheaton | 24 | ||||
| 9/28/2019 | Elmhurst | 32 | at | Carroll WI | 30 | |||
| Washington U | 21 | at | Carthage | 10 | ||||
| Augustana IL | 17 | at | Illinois Wesleyan | 21 | ||||
| Wheaton | 62 | at | Millikin | 0 | ||||
| North Park | 0 | at | North Central | 77 | ||||
| 10/5/2019 | Millikin | 14 | at | Augustana IL | 40 | |||
| Carthage | 38 | at | Elmhurst | 14 | ||||
| Carroll WI | 14 | at | Illinois Wesleyan | 42 | ||||
| North Park | 10 | at | Washington U | 35 | ||||
| North Central | 21 | at | Wheaton | 35 | ||||
| 10/12/2019 | Millikin | 30 | at | Carroll WI | 7 | |||
| Illinois Wesleyan | 31 | at | Carthage | 7 | ||||
| Augustana IL | 14 | at | North Central | 42 | ||||
| Wheaton | 63 | at | North Park | 0 | ||||
| Elmhurst | 7 | at | Washington U | 47 | ||||
| 10/19/2019 | North Park | 0 | at | Augustana IL | 71 | |||
| North Central | 62 | at | Carroll WI | 3 | ||||
| Illinois Wesleyan | 43 | at | Elmhurst | 0 | ||||
| Carthage | 53 | at | Millikin | 50 | ||||
| Washington U | 13 | at | Wheaton | 52 | ||||
| 10/26/2019 | Washington U | 21 | at | Illinois Wesleyan | 0 | |||
| Elmhurst | 0 | at | Millikin | 34 | ||||
| Carthage | 6 | at | North Central | 49 | ||||
| Carroll WI | 26 | at | North Park | 14 | ||||
| Augustana IL | 0 | at | Wheaton | 40 | ||||
| 11/2/2019 | Wheaton | 51 | at | Carroll WI | 12 | |||
| North Park | 14 | at | Carthage | 46 | ||||
| North Central | 82 | at | Elmhurst | 7 | ||||
| Millikin | 12 | at | Illinois Wesleyan | 40 | ||||
| Augustana IL | 14 | at | Washington U | 35 | ||||
| 11/9/2019 | Carroll WI | 6 | at | Augustana IL | 34 | |||
| Illinois Wesleyan | 14 | at | North Central | 69 | ||||
| Elmhurst | 14 | at | North Park | 38 | ||||
| Millikin | 35 | at | Washington U | 28 | OT | |||
| Carthage | 6 | at | Wheaton | 55 | ||||
| 11/16/2019 | Washington U | 62 | at | Carroll WI | 14 | |||
| Augustana IL | 51 | at | Carthage | 36 | ||||
| Wheaton | 58 | at | Elmhurst | 0 | ||||
| North Park | 6 | at | Illinois Wesleyan | 32 | ||||
| North Central | 59 | at | Millikin | 32 | ||||
| 11/23/2019 | Wabash | 15 | at | North Central | 51 | D3 Playoff round 1 | NCA | |
| Martin Luther | 7 | at | Wheaton | 51 | D3 Playoff round 1 | UMWAC | ||
| 11/30/2019 | North Central | 59 | at | Mount Union | 52 | D3 Playoff round 2 | @ OAC | |
| Central IA | 13 | at | Wheaton | 49 | D3 Playoff round 2 | ARC | ||
| 12/7/2019 | Delaware Valley | 14 | at | North Central | 31 | D3 Quarterfinals | MidAC | |
| St John's MN | 34 | at | Wheaton | 33 | D3 Quarterfinals | MIA | ||
| 12/14/2019 | North Central | 45 | at | Muhlenberg | 14 | D3 Semifinal | @ Cen | |
| 12/20/2019 | Wisconsin-Whitewater | 14 | vs | North Central | 41 | D3 Championship - Shenandoah TX | vs WIAC |