Estádio: Rosenbloom Field Round: 1
| NCAAF | 2022/10/29 18:00 | Chicago Maroons v Grinnell Pioneers | L | 58-0 |
| NCAAF | 2021/10/30 18:00 | Grinnell Pioneers v Chicago Maroons | L | 3-78 |
| NCAAF | 2023/10/28 18:00 | Illinois College Blueboys v Grinnell Pioneers | L | 93-0 |
| NCAAF | 2023/10/21 18:00 | Grinnell Pioneers v Knox Prairie Fire | L | 7-14 |
| NCAAF | 2023/10/14 18:00 | Lake Forest Foresters v Grinnell Pioneers | L | 47-0 |
| NCAAF | 2023/10/07 19:00 | Monmouth Scots v Grinnell Pioneers | L | 69-6 |
| NCAAF | 2023/09/30 18:00 | Grinnell Pioneers v Lawrence Vikings | W | 34-16 |
| NCAAF | 2023/09/16 18:00 | Beloit Buccaneers v Grinnell Pioneers | W | 23-33 |
| NCAAF | 2023/09/09 18:00 | Grinnell Pioneers v Ripon Red Hawks | L | 12-31 |
| NCAAF | 2023/09/02 23:00 | Lyon College Scots v Grinnell Pioneers | L | 18-12 |
| NCAAF | 2023/10/28 18:00 | Chicago Maroons v Lawrence Vikings | W | 55-12 |
| NCAAF | 2023/10/21 18:00 | Cornell Rams v Chicago Maroons | L | 47-34 |
| NCAAF | 2023/10/14 19:00 | Chicago Maroons v Ripon Red Hawks | W | 21-6 |
| NCAAF | 2023/10/07 18:00 | Chicago Maroons v Illinois College Blueboys | L | 20-41 |
| NCAAF | 2023/09/30 18:00 | Beloit Buccaneers v Chicago Maroons | W | 7-48 |
| NCAAF | 2023/09/16 19:00 | Chicago Maroons v Knox Prairie Fire | W | 63-0 |
| NCAAF | 2023/09/09 18:00 | Monmouth Scots v Chicago Maroons | L | 39-6 |
| NCAAF | 2023/09/02 18:00 | Chicago Maroons v Claremont-M-S | L | 15-24 |