Stadium: Rosenbloom Field Round: 1
| 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 |
| NCAAF | 2019/10/19 18:00 | Cornell Rams v Chicago Maroons | W | 7-56 |
| NCAAF | 2019/10/12 19:00 | Chicago Maroons v Knox Prairie Fire | W | 37-6 |
| NCAAF | 2019/10/05 18:00 | Beloit Buccaneers v Chicago Maroons | W | 0-48 |
| NCAAF | 2019/09/28 18:00 | Chicago Maroons v Lake Forest Foresters | W | 27-10 |
| NCAAF | 2019/09/14 18:00 | Simpson Storm v Chicago Maroons | L | 27-23 |
| NCAAF | 2019/09/07 23:00 | Chicago Maroons v Washington Bears | L | 7-43 |
| NCAAF | 2018/11/03 18:00 | Macalester Scots v Chicago Maroons | W | 21-28 |
| NCAAF | 2018/10/27 19:00 | Chicago Maroons v Ripon Red Hawks | W | 35-6 |