Stadium: Rosenbloom Field Round: 1
| NCAAF | 2021/10/23 18:00 | Lake Forest Foresters v Grinnell Pioneers | L | 79-0 |
| NCAAF | 2021/10/16 18:00 | Grinnell Pioneers v Knox Prairie Fire | L | 28-49 |
| NCAAF | 2021/10/09 18:00 | Grinnell Pioneers v Ripon Red Hawks | L | 8-52 |
| NCAAF | 2021/10/02 18:00 | Beloit Buccaneers v Grinnell Pioneers | W | 13-40 |
| NCAAF | 2021/09/18 18:00 | Grinnell Pioneers v Lawrence Vikings | W | 35-28 |
| NCAAF | 2021/09/11 19:00 | Monmouth Scots v Grinnell Pioneers | L | 42-7 |
| NCAAF | 2021/09/04 18:00 | Rockford Regents v Grinnell Pioneers | L | 48-13 |
| NCAAF | 2019/09/28 18:00 | Grinnell Pioneers v Macalester Scots | L | 3-42 |
| NCAAF | 2021/10/23 19:00 | Chicago Maroons v Ripon Red Hawks | W | 38-14 |
| NCAAF | 2021/10/16 18:00 | Cornell Rams v Chicago Maroons | W | 21-47 |
| NCAAF | 2021/10/09 18:00 | Monmouth Scots v Chicago Maroons | L | 40-37 |
| NCAAF | 2021/10/02 19:00 | Chicago Maroons v Knox Prairie Fire | W | 45-10 |
| NCAAF | 2021/09/18 18:00 | Beloit Buccaneers v Chicago Maroons | W | 0-66 |
| NCAAF | 2021/09/11 18:00 | Chicago Maroons v Illinois College Blueboys | W | 66-14 |
| NCAAF | 2021/09/04 18:00 | Chicago Maroons v Washington Bears | W | 31-21 |
| NCAAF | 2019/11/09 19:00 | Illinois College Blueboys v Chicago Maroons | W | 14-20 |