Stadium: Johnson Center Round: 1
| NCAAB | 2019/02/14 00:00 | Simmons College (Ky) v Oakland City | W | 67-75 |
| NCAAB | 2019/01/26 21:00 | Oakland City v Simmons College (Ky) | W | 92-63 |
| NCAAB | 2020/01/18 19:00 | Midway v Oakland City | L | 92-86 |
| NCAAB | 2020/01/11 21:00 | Oakland City v Wilberforce | L | 85-91 |
| NCAAB | 2019/12/18 01:00 | Brescia (KY) v Oakland City | L | 112-94 |
| NCAAB | 2019/12/15 21:00 | Oakland City v Ohio University Chillcothe Hilltoppers | W | 108-76 |
| NCAAB | 2019/12/14 21:00 | Oakland City v Ohio University Chillcothe Hilltoppers | W | 110-61 |
| NCAAB | 2019/12/12 01:00 | Oakland City v Campbellsville University Somerset | W | 104-103 |
| 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 | 2019/02/14 00:00 | Simmons College (Ky) v Oakland City | L | 67-75 |
| NCAAB | 2019/01/26 21:00 | Oakland City v Simmons College (Ky) | L | 92-63 |