Stadium: Sam Greeley Field Round: 1
| NCAAF | 2019/11/16 18:00 | Rockford Regents v Eureka Red Devils | L | 28-38 |
| NCAAF | 2019/11/10 00:00 | Rockford Regents v Concordia Chicago Cougars | L | 25-28 |
| NCAAF | 2019/11/02 18:00 | Concordia Wisconsin Falcons v Rockford Regents | L | 41-27 |
| NCAAF | 2019/10/26 18:00 | Aurora Spartans v Rockford Regents | L | 56-14 |
| NCAAF | 2019/10/19 18:00 | Rockford Regents v Lakeland Muskies | L | 21-76 |
| NCAAF | 2019/10/12 18:00 | Benedictine Eagles v Rockford Regents | L | 48-13 |
| NCAAF | 2019/10/05 18:00 | Rockford Regents v Wisconsin Lutheran Warriors | L | 13-27 |
| NCAAF | 2019/09/21 18:00 | Alma College Scots v Rockford Regents | L | 51-16 |
| NCAAF | 2019/09/28 18:00 | Grinnell Pioneers v Macalester Scots | L | 3-42 |
| NCAAF | 2019/09/14 18:00 | Lake Forest Foresters v Grinnell Pioneers | L | 44-0 |
| NCAAF | 2019/09/07 18:00 | Grinnell Pioneers v Lawrence Vikings | L | 0-28 |
| NCAAF | 2018/11/03 18:00 | Grinnell Pioneers v Cornell Rams | L | 13-23 |
| NCAAF | 2018/10/27 18:00 | Illinois College Blueboys v Grinnell Pioneers | L | 55-14 |
| NCAAF | 2018/10/20 17:00 | Grinnell Pioneers v Lake Forest Foresters | L | 0-24 |
| NCAAF | 2018/10/13 18:00 | Grinnell Pioneers v Knox Prairie Fire | L | 7-28 |
| NCAAF | 2018/10/06 19:00 | Monmouth Scots v Grinnell Pioneers | L | 55-0 |