Stadium: Schneider Stadium Round: 1
| NCAAF | 2019/11/09 19:00 | Augustana Augie v Carroll Pioneers | L | 34-6 |
| NCAAF | 2019/11/02 18:00 | Carroll Pioneers v Wheaton Thunder | L | 12-51 |
| NCAAF | 2019/10/26 18:00 | North Park Vikings v Carroll Pioneers | W | 14-26 |
| NCAAF | 2019/10/19 18:00 | Carroll Pioneers v North Central Illinois | L | 3-62 |
| NCAAF | 2019/10/12 19:00 | Carroll Pioneers v Millikin Big Blue | L | 7-30 |
| NCAAF | 2019/10/05 18:00 | Illinois Wesleyan Titans v Carroll Pioneers | L | 42-14 |
| NCAAF | 2019/09/28 18:00 | Carroll Pioneers v Elmhurst Bluejays | L | 30-32 |
| NCAAF | 2019/09/21 17:00 | Carthage Red Men v Carroll Pioneers | L | 36-7 |
| 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 |
| NCAAF | 2019/09/21 22:00 | Washington Bears v North Central Illinois | L | 13-46 |