Stadium: Owensboro Sports Center Round: 1
| NCAAB | 2020/01/17 00:30 | Hillsdale Chargers v Kentucky Wesleyan | L | 72-60 |
| NCAAB | 2019/03/02 20:00 | Hillsdale Chargers v Kentucky Wesleyan | W | 61-76 |
| NCAAB | 2019/01/25 01:45 | Kentucky Wesleyan v Hillsdale Chargers | L | 47-57 |
| NCAAB | 2020/02/07 01:45 | Kentucky Wesleyan v Findlay | L | 56-59 |
| NCAAB | 2020/02/01 18:00 | Lake Erie v Kentucky Wesleyan | L | 71-62 |
| NCAAB | 2020/01/24 01:45 | Kentucky Wesleyan v Lake Erie | W | 65-51 |
| NCAAB | 2020/01/18 20:00 | Findlay v Kentucky Wesleyan | L | 89-71 |
| NCAAB | 2020/01/17 00:30 | Hillsdale Chargers v Kentucky Wesleyan | L | 72-60 |
| NCAAB | 2020/01/11 20:15 | Kentucky Wesleyan v Alderson-Broaddus Battlers | L | 83-85 |
| NCAAB | 2020/01/10 01:45 | Kentucky Wesleyan v Ohio Valley | W | 75-70 |
| NCAAB | 2020/01/04 20:00 | Malone v Kentucky Wesleyan | W | 73-81 |
| NCAAB | 2020/02/07 00:45 | Trevecca Nazarene v Hillsdale Chargers | W | 59-72 |
| NCAAB | 2020/02/01 20:00 | Hillsdale Chargers v Malone | W | 75-68 |
| NCAAB | 2020/01/25 20:00 | Malone v Hillsdale Chargers | W | 60-81 |
| NCAAB | 2020/01/24 00:30 | Walsh v Hillsdale Chargers | L | 67-62 |
| NCAAB | 2020/01/18 20:00 | Hillsdale Chargers v Trevecca Nazarene | W | 75-56 |
| NCAAB | 2020/01/17 00:30 | Hillsdale Chargers v Kentucky Wesleyan | W | 72-60 |
| NCAAB | 2020/01/11 18:00 | Ohio Dominican v Hillsdale Chargers | L | 77-64 |
| NCAAB | 2020/01/10 00:30 | Tiffin Dragons v Hillsdale Chargers | W | 71-95 |