Stadium: Stagg Field Round: 1
| NCAAF | 2019/09/07 23:00 | Chicago Maroons v Washington Bears | L | 7-43 |
| NCAAF | 2018/09/01 23:00 | Washington Bears v Chicago Maroons | L | 24-17 |
| 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 | 2019/09/07 23:00 | Chicago Maroons v Washington Bears | L | 7-43 |
| NCAAF | 2019/11/16 19:00 | Carroll Pioneers v Washington Bears | W | 14-62 |
| NCAAF | 2019/11/09 19:00 | Washington Bears v Millikin Big Blue | L | 28-35 |
| NCAAF | 2019/11/02 18:00 | Washington Bears v Augustana Augie | W | 35-14 |
| NCAAF | 2019/10/26 18:00 | Illinois Wesleyan Titans v Washington Bears | W | 0-21 |
| NCAAF | 2019/10/19 23:00 | Wheaton Thunder v Washington Bears | L | 52-13 |
| NCAAF | 2019/10/12 18:00 | Washington Bears v Elmhurst Bluejays | W | 47-7 |
| NCAAF | 2019/10/05 18:00 | Washington Bears v North Park Vikings | W | 35-10 |
| NCAAF | 2019/09/28 17:00 | Carthage Red Men v Washington Bears | W | 10-21 |