Stadium: Dawn Tibbetts Potter Arena Round: 1
| NCAAB | 2019/11/08 17:30 | Hillsdale Chargers v Southern Indiana | L | 73-82 |
| NCAAB | 2019/03/02 20:00 | Hillsdale Chargers v Kentucky Wesleyan | L | 61-76 |
| NCAAB | 2019/02/22 00:30 | Ohio Valley v Hillsdale Chargers | W | 48-79 |
| NCAAB | 2019/02/02 20:00 | Hillsdale Chargers v Cedarville | W | 79-66 |
| NCAAB | 2019/01/25 01:45 | Kentucky Wesleyan v Hillsdale Chargers | W | 47-57 |
| NCAAB | 2019/01/11 00:30 | Hillsdale Chargers v Ohio Valley | W | 80-60 |
| NCAAB | 2019/01/05 17:00 | Davis & Elkins v Hillsdale Chargers | W | 60-69 |
| NCAAB | 2019/01/04 00:30 | Alderson-Broaddus Battlers v Hillsdale Chargers | L | 64-63 |
| NCAAB | 2019/11/08 19:30 | Malone v Oakland City | L | 93-77 |
| NCAAB | 2019/11/06 02:00 | Austin Peay v Oakland City | L | 110-67 |
| NCAAB | 2019/02/24 21:00 | Oakland City v Andrews Cardinals | W | 71-64 |
| NCAAB | 2019/02/16 19:00 | Appalachian Bible Warriors v Oakland City | W | 78-96 |
| NCAAB | 2019/02/14 00:00 | Simmons College (Ky) v Oakland City | W | 67-75 |
| NCAAB | 2019/02/10 21:00 | Oakland City v Wright St Lake | W | 112-73 |
| NCAAB | 2019/02/09 21:00 | Oakland City v Wright St Lake | W | 109-59 |
| NCAAB | 2019/02/07 01:00 | Oakland City v East-West University | W | 105-76 |