Stadium: Stagg Field Round: 1
| NCAAF | 2023/11/04 18:00 | Grinnell Pioneers v Chicago Maroons | W | 14-48 |
| NCAAF | 2022/10/29 18:00 | Chicago Maroons v Grinnell Pioneers | W | 58-0 |
| NCAAF | 2021/10/30 18:00 | Grinnell Pioneers v Chicago Maroons | W | 3-78 |
| NCAAF | 2024/11/02 22:00 | Lawrence Vikings v Chicago Maroons | W | 14-64 |
| NCAAF | 2024/10/26 19:00 | Chicago Maroons v Cornell Rams | W | 33-14 |
| NCAAF | 2024/10/19 18:00 | Ripon Red Hawks v Chicago Maroons | W | 6-30 |
| NCAAF | 2024/10/12 23:00 | Illinois College Blueboys v Chicago Maroons | L | 50-37 |
| NCAAF | 2024/10/05 18:00 | Chicago Maroons v Beloit Buccaneers | W | 23-3 |
| NCAAF | 2024/09/21 18:00 | Knox Prairie Fire v Chicago Maroons | W | 13-27 |
| NCAAF | 2024/09/14 18:00 | Chicago Maroons v Monmouth Scots | L | 21-34 |
| NCAAF | 2024/09/07 17:00 | Claremont-M-S v Chicago Maroons | L | 24-0 |
| NCAAF | 2024/11/02 18:00 | Grinnell Pioneers v Illinois College Blueboys | L | 14-56 |
| NCAAF | 2024/10/26 18:00 | Knox Prairie Fire v Grinnell Pioneers | W | 14-21 |
| NCAAF | 2024/10/19 18:00 | Grinnell Pioneers v Lake Forest Foresters | L | 22-42 |
| NCAAF | 2024/10/12 18:00 | Grinnell Pioneers v Monmouth Scots | L | 7-49 |
| NCAAF | 2024/10/05 17:00 | Lawrence Vikings v Grinnell Pioneers | W | 14-17 |
| NCAAF | 2024/09/21 18:00 | Grinnell Pioneers v Beloit Buccaneers | L | 7-16 |
| NCAAF | 2024/09/14 18:00 | Ripon Red Hawks v Grinnell Pioneers | L | 23-19 |
| NCAAF | 2024/09/07 18:00 | Grinnell Pioneers v Lyon College Scots | L | 28-48 |