Stadium: Owensboro Sports Center Round: 1
| NCAAB | 2019/11/19 01:00 | Southern Indiana v Kentucky Wesleyan | L | 82-63 |
| NCAAB | 2019/11/16 20:15 | Kentucky Wesleyan v Urbana Blue Knights | L | 53-56 |
| NCAAB | 2019/11/14 00:00 | Bellarmine v Kentucky Wesleyan | L | 90-51 |
| NCAAB | 2019/11/08 00:30 | Samford v Kentucky Wesleyan | L | 68-42 |
| NCAAB | 2019/03/02 20:00 | Hillsdale Chargers v Kentucky Wesleyan | W | 61-76 |
| NCAAB | 2019/03/01 00:30 | Findlay v Kentucky Wesleyan | L | 81-59 |
| NCAAB | 2019/02/23 20:00 | Kentucky Wesleyan v Alderson-Broaddus Battlers | L | 68-82 |
| NCAAB | 2019/02/22 00:30 | Kentucky Wesleyan v Davis & Elkins | W | 92-89 |
| 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 | 2019/11/06 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 |