| Date | Location | Result | |
| 03/21/21 | Hiram, OH | Ohio Wesleyan 70, Hiram 55 | |
| 3/18/21 | Branch Rickey Arena; | Ohio Wesleyan 78, Hiram 39 | |
| 03/13/21 | Hiram, OH | Hiram 68, Wooster 58 | |
| 03/12/21 | Wooster, OH | Hiram 76, Wooster 71 | |
| 03/06/21 | Delaware, OH | Ohio Wesleyan 84, Wooster 32 | |
| 03/06/21 | Granville, OH | Wittenberg 61, Denison 58 | |
| 03/05/21 | Springfield, OH | Wittenberg 76, Denison 56 | |
| 03/04/21 | Wooster, OH | Ohio Wesleyan 90, Wooster 57 | |
| 03/03/21 | Jacksonville, IL | DePauw 74, Illinois Col. 35 | |
| 2/28/21 | Branch Rickey Arena; | DePauw 57, Ohio Wesleyan 41 | |
| 02/27/21 | Wooster, OH | Wittenberg 62, Wooster 55 | |
| 02/26/21 | Springfield, OH | Wittenberg 69, Wooster 51 | |
| 02/26/21 | Greencastle, IN | DePauw 76, Ohio Wesleyan 53 | |
| 02/20/21 | Granville, OH | Denison 57, Wooster 46 | |
| 02/20/21 | Springfield, OH | Wittenberg 41, DePauw 37 | |
| 02/19/21 | Wooster, OH | Denison 77, Wooster 58 | |
| 02/18/21 | Greencastle, IN | DePauw 48, Wittenberg 41 | |
| 2/13/21 | Branch Rickey Arena; | Ohio Wesleyan 72, Wittenberg 60 | |
| 02/13/21 | Greencastle, IN | DePauw 67, Denison 61 | |
| 2/12/21 | Springfield, OH | Ohio Wesleyan 55, Wittenberg 44 | |
| 02/11/21 | Granville, OH | DePauw 62, Denison 41 | |
| 2/6/21 | Branch Rickey Arena; | Ohio Wesleyan 57, Denison 52 | |
| 02/05/21 | Granville, OH | Ohio Wesleyan 65, Denison 62 | |
| 01/30/21 | Greencastle, IN | DePauw 74, Greenville 41 | |
| 01/29/21 | Greencastle, IN | DePauw 74, Greenville 44 |