| Date | Location | Result | |
| 03/06/20 | Timken Gymnasium; Wooster, Ohio | Grove City 67, College of Wooster 62 | Box score |
| 02/29/20 | Pam Evans Smith Arena; Springfield, Ohio | College of Wooster 87, Wittenberg Univ. 63 | Box score |
| 02/28/20 | Pam Evans Smith Arena; Springfield, Ohio | College of Wooster 74, Denison University 62 | Box score |
| 02/25/20 | Timken Gymnasium; Wooster, Ohio | College of Wooster 92, Allegheny College 66 | Box score |
| 02/22/20 | Timken Gymnasium; Wooster, Ohio | DePauw University 88, College of Wooster 87 (OT) | Box score |
| 02/19/20 | Philips Gymnasium; Oberlin, Ohio | College of Wooster 57, Oberlin College 53 | Box score |
| 2/15/20 | Pam Evans Smith Arena; Springfield, Ohio | Wittenberg Univ. 88, College of Wooster 81 | Box score |
| 02/12/20 | Timken Gymnasium; Wooster, Ohio | College of Wooster 93, Denison University 72 | Box score |
| 02/08/20 | Timken Gymnasium; Wooster, Ohio | College of Wooster 80, Ohio Wesleyan Univ. 71 | Box score |
| 02/05/20 | Timken Gymnasium; Wooster, Ohio | College of Wooster 76, Kenyon College 57 | Box score |
| 02/01/20 | Chadwick Court; Crawfordsville, Ind. | Wabash College 68, College of Wooster 67 | Box score |
| 01/29/20 | Timken Gymnasium; Wooster, Ohio | Allegheny College 89, College of Wooster 84 | Box score |
| 01/25/20 | Price Gymnasium; Hiram, OHio | College of Wooster 98, Hiram College 76 | Box score |
| 01/22/20 | Livingston Gymnasium; Granville, Ohio | Denison University 72, College of Wooster 71 | Box score |
| 01/18/20 | Timken Gymnasium; Wooster, Ohio | College of Wooster 98, Wittenberg Univ. 86 | Box score |
| 01/15/20 | Timken Gymnasium; Wooster, Ohio | College of Wooster 94, Oberlin College 92 | Box score |
| 01/11/20 | Neal Fieldhouse; Greencastle, Ind. | College of Wooster 70, DePauw University 68 | Box score |
| 01/08/20 | Tomsich Arena; Gambier, Ohio | College of Wooster 83, Kenyon College 61 | Box score |
| 01/04/20 | Branch Rickey Arena; Delaware, Ohio | Ohio Wesleyan Univ. 65, College of Wooster 60 | Box score |
| 12/29/19 | Timken Gymnasium; Wooster, Ohio | College of Wooster 87, Whitworth University 82 | Box score |
| 12/28/19 | Timken Gymnasium; Wooster, Ohio | College of Wooster 93, Keene State College 76 | Box score |
| 12/16/19 | DME Sports Academy; Daytona Beach, Fla. | College of Wooster 94, College at Brockport 90 | Box score |
| 12/15/19 | DME Sports Academy; Daytona Beach, Fla. | College of Wooster 81, St. John Fisher College 80 | Box score |
| 12/07/19 | Timken Gymnasium; Wooster, Ohio | College of Wooster 79, Wabash College 74 | Box score |
| 12/04/19 | David V. Wise Center; Meadville, Pa. | College of Wooster 62, Allegheny College 61 | Box score |
| 11/27/19 | Timken Gymnasium; Wooster, Ohio | Univ. of Mount Union 81, College of Wooster 67 | Box score |
| 11/23/19 | Timken Gymnasium; Wooster, Ohio | College of Wooster 86, Wilmington College 65 | Box score |
| 11/20/19 | Timken Gymnasium; Wooster, Ohio | College of Wooster 98, Hiram College 70 | Box score |
| 11/12/19 | Timken Gymnasium; Wooster, Ohio | College of Wooster 110, Medaille College 100 | Box score |