Stadium: Johnson Center Round: 1
| NCAAB | 2019/12/07 21:00 | Oakland City v Illinois Springfield | L | 71-108 |
| 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 | 2019/11/26 17:00 | Kentucky State v Campbellsville University Somerset | L | 107-80 |
| NCAAB | 2019/11/17 00:30 | Berea v Campbellsville University Somerset | L | 82-71 |
| NCAAB | 2019/11/09 23:00 | Bluefield State Big Blues v Campbellsville University Somerset | L | 120-76 |
| NCAAB | 2018/12/08 21:00 | Oakland City v Campbellsville University Somerset | L | 102-76 |