| Date | Location | Result | |
| 03-10-20 | Rock Hill, SC (Winthrop Coliseum) | Upstate 60, Winthrop 57 | Box score |
| 03-07-20 | Rock Hill, SC (Winthrop Coliseum) | Upstate 66, Winthrop 59 | Box score |
| 03-04-20 | Clinton, SC (Templeton Center) | Presbyterian 88, Winthrop 54 | Box score |
| 02-29-20 | Rock Hill, SC (Winthrop Coliseum) | Radford 56, Winthrop 50 | Box score |
| 02-25-20 | Farmville, VA (Willett Hall) | Winthrop 63, Longwood 60 | Box score |
| 02-22-20 | Rock Hill, SC (Winthrop Coliseum) | Gardner-Webb 54, Winthrop 49 | Box score |
| 02-18-20 | Rock Hill, SC (Winthrop Coliseum) | Campbell 61, Winthrop 58 | Box score |
| 02-15-20 | Asheville, NC (Kimmel Arena) | UNC Asheville 65, Winthrop 55 | Box score |
| 02-11-20 | Hampton, VA (Hampton Convocation Center) | Hampton 62, Winthrop 48 | Box score |
| 02-04-20 | Rock Hill, SC (Winthrop Coliseum) | Winthrop 56, Charleston Southern 46 | Box score |
| 02-01-20 | High Point, NC (Millis Hall) | High Point 94, Winthrop 61 | Box score |
| 01-28-20 | Rock Hill, SC (Winthrop Coliseum) | AVL 50, Winthrop 43 | Box score |
| 01-25-20 | North Charleston, SC (CSU Field House) | Winthrop 58, Charleston So. 53 | Box score |
| 01-21-20 | Rock Hill, SC (Winthrop Coliseum) | Winthrop 74, Longwood 63 | Box score |
| 01-18-20 | Radford, Va. (Dedmon Center) | Radford 54, Winthrop 53 | Box score |
| 01-14-20 | Buies Creek, N.C. (Gore Arena) | Campbell 63, Winthrop 47 | Box score |
| 01-11-20 | Rock Hill, SC (Winthrop Coliseum) | Winthrop 61, Presbyterian 54 | Box score |
| 01-09-20 | Spartanburg, SC (G.B. Hodge Center) | Winthrop 52, USC Upstate 38 | Box score |
| 01-06-20 | Boiling Springs, NC / Paul Porter Arena | Gardner-Webb 71, Winthrop 59 | Box score |
| 12-31-19 | Rock Hill, SC (Winthrop Coliseum) | Winthrop 69, HPUWBB 63 | Box score |
| 12-28-19 | Rock Hill, SC (Winthrop Coliseum) | Winthrop 72, Hampton 66 | Box score |
| 12-21-19 | Cullowhee, NC (Ramsey Center) | Winthrop 63, Western Caro. 60 | Box score |
| 12-17-19 | Wilmington, NC (Trask Coliseum) | Winthrop 75, UNCW 63 | Box score |
| 12-11-19 | Lexington, KY (Memorial Coliseum) | Kentucky 91, Winthrop 36 | Box score |
| 12-01-19 | Rock Hill, SC (Winthrop Coliseum) | COFC 84, Winthrop 73 | Box score |
| 11-26-19 | Rock Hill, SC (Winthrop Coliseum) | Georgia Southern 91, Winthrop 47 | Box score |
| 11-23-19 | Spartanburg, SC (Converse College) | Wofford 60, Winthrop 59 | Box score |
| 11-20-19 | Norfolk, V.A. (Chartway Arena) | OLD DOMINION 68, Winthrop 44 | Box score |
| 11-12-19 | Durham, NC (McDougald-McLendon Arena) | Winthrop 56, N.C. Central 46 | Box score |
| 11-09-19 | Rock Hill, SC (Winthrop Coliseum) | Iona 68, Winthrop 61 | Box score |