Stadium: Stagg Field Round: 1
| NCAAF | 2019/11/09 19:00 | Illinois College Blueboys v Chicago Maroons | W | 14-20 |
| NCAAF | 2018/09/22 18:00 | Chicago Maroons v Illinois College Blueboys | W | 56-9 |
| 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 |
| NCAAF | 2019/11/02 18:00 | Chicago Maroons v Monmouth Scots | L | 20-21 |
| 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 | 2021/09/02 23:00 | Illinois College Blueboys v Lakeland Muskies | L | 18-28 |
| NCAAF | 2019/11/09 19:00 | Illinois College Blueboys v Chicago Maroons | L | 14-20 |
| NCAAF | 2019/10/26 18:00 | Illinois College Blueboys v Knox Prairie Fire | W | 47-17 |
| NCAAF | 2019/10/19 19:00 | Monmouth Scots v Illinois College Blueboys | L | 30-15 |
| NCAAF | 2019/10/12 18:00 | Illinois College Blueboys v Cornell Rams | W | 56-17 |
| NCAAF | 2019/10/05 18:00 | Lawrence Vikings v Illinois College Blueboys | W | 10-55 |
| NCAAF | 2019/09/28 18:00 | Illinois College Blueboys v Ripon Red Hawks | W | 28-25 |
| NCAAF | 2019/09/14 18:00 | Nebraska Wesleyan Prairie Wolves v Illinois College Blueboys | L | 25-20 |