Stadium: Strong Stadium Round: 1
| NCAAF | 2019/09/28 18:00 | Knox Prairie Fire v Beloit Buccaneers | L | 45-21 |
| NCAAF | 2019/09/14 18:00 | Crown Storm v Beloit Buccaneers | L | 23-6 |
| NCAAF | 2019/09/07 22:00 | Beloit Buccaneers v Concordia Chicago Cougars | L | 6-44 |
| NCAAF | 2018/11/03 18:00 | Beloit Buccaneers v St Norbert Green Knights | L | 0-60 |
| NCAAF | 2018/10/27 18:00 | Lawrence Vikings v Beloit Buccaneers | L | 32-27 |
| NCAAF | 2018/10/20 18:00 | Beloit Buccaneers v Chicago Maroons | L | 0-63 |
| NCAAF | 2018/10/13 18:00 | Ripon Red Hawks v Beloit Buccaneers | L | 49-14 |
| NCAAF | 2018/10/06 18:00 | Beloit Buccaneers v Macalester Scots | L | 26-42 |
| 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 | 2019/09/07 23:00 | Chicago Maroons v Washington Bears | L | 7-43 |
| NCAAF | 2018/11/03 18:00 | Macalester Scots v Chicago Maroons | W | 21-28 |
| NCAAF | 2018/10/27 19:00 | Chicago Maroons v Ripon Red Hawks | W | 35-6 |
| NCAAF | 2018/10/20 18:00 | Beloit Buccaneers v Chicago Maroons | W | 0-63 |
| NCAAF | 2018/10/13 18:00 | Chicago Maroons v St Norbert Green Knights | L | 20-21 |
| NCAAF | 2018/10/06 18:00 | Lawrence Vikings v Chicago Maroons | W | 0-49 |