Stadium: England Stadium Round: 1
| NCAAF | 2021/10/30 18:00 | Cornell Rams v Illinois College Blueboys | W | 7-39 |
| NCAAF | 2021/10/23 18:00 | Illinois College Blueboys v Knox Prairie Fire | W | 27-20 |
| NCAAF | 2021/10/16 18:00 | Lawrence Vikings v Illinois College Blueboys | W | 37-38 |
| NCAAF | 2021/10/09 18:00 | Illinois College Blueboys v Lake Forest Foresters | L | 13-48 |
| NCAAF | 2021/10/02 18:00 | Ripon Red Hawks v Illinois College Blueboys | L | 24-13 |
| NCAAF | 2021/09/18 18:00 | Illinois College Blueboys v Monmouth Scots | L | 27-37 |
| NCAAF | 2021/09/11 18:00 | Chicago Maroons v Illinois College Blueboys | L | 66-14 |
| NCAAF | 2021/09/02 23:00 | Illinois College Blueboys v Lakeland Muskies | L | 18-28 |
| NCAAF | 2021/10/30 18:00 | Grinnell Pioneers v Chicago Maroons | L | 3-78 |
| 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 |