Stadium: Johnson Center Round: 1
| NCAAB | 2019/11/29 23:00 | Campbellsville Tigers v Oakland City | L | 106-69 |
| NCAAB | 2019/11/27 01:30 | Southern Indiana v Oakland City | L | 121-58 |
| NCAAB | 2019/11/23 20:00 | Wilberforce v Oakland City | L | 98-90 |
| NCAAB | 2019/11/21 01:00 | Kentucky Wesleyan v Oakland City | L | 100-68 |
| NCAAB | 2019/11/16 21:00 | Oakland City v Welch Flames | W | 96-89 |
| NCAAB | 2019/11/12 23:00 | Rose-Hulman Tech v Oakland City | L | 98-90 |
| NCAAB | 2019/11/10 00:00 | Hillsdale Chargers v Oakland City | L | 105-54 |
| NCAAB | 2019/11/08 19:30 | Malone v Oakland City | L | 93-77 |
| NCAAB | 2019/12/04 01:30 | Illinois Springfield v Lewis | L | 64-71 |
| NCAAB | 2019/11/29 20:00 | Illinois St v Illinois Springfield | L | 76-57 |
| NCAAB | 2019/11/28 00:00 | Northwest Missouri State v Illinois Springfield | L | 91-56 |
| NCAAB | 2019/11/16 00:00 | Purdue Northwest v Illinois Springfield | W | 85-97 |
| NCAAB | 2019/11/13 01:00 | Illinois Springfield v St Louis Pharmacist | W | 90-61 |
| NCAAB | 2019/11/10 01:30 | Illinois Springfield v Wisconsin-Parkside | W | 78-70 |
| NCAAB | 2019/11/09 01:30 | Illinois Springfield v Ohio Valley | W | 91-71 |
| NCAAB | 2019/03/02 21:00 | Illinois Springfield v Bellarmine | L | 59-90 |