Stadium: Winthrop Coliseum Round: 1
Home Manager: Pat Kelsey Away Manager: Barclay Radebaugh
| NCAAB | 2019/02/08 00:30 | Winthrop v Charleston Southern | L | 76-72 |
| NCAAB | 2018/02/24 19:00 | Charleston Southern v Winthrop | W | 78-75 |
| NCAAB | 2018/01/13 00:30 | Charleston Southern v Winthrop | L | 53-64 |
| NCAAB | 2017/03/03 00:00 | Charleston Southern v Winthrop | L | 78-92 |
| NCAAB | 2017/02/23 23:30 | Charleston Southern v Winthrop | L | 72-86 |
| NCAAB | 2016/12/30 00:30 | Charleston Southern v Winthrop | L | 68-84 |
| NCAAB | 2016/01/28 00:00 | Winthrop v Charleston Southern | L | 97-72 |
| NCAAB | 2015/12/03 00:30 | Charleston Southern v Winthrop | L | 82-83 |
| NCAAB | 2015/02/03 01:00 | Winthrop v Charleston Southern | L | 77-55 |
| NCAAB | 2014/02/15 12:00 | Charleston Southern v Winthrop | W | 84-64 |
| NCAAB | 2014/01/11 12:00 | Winthrop v Charleston Southern | L | 85-68 |
| NCAAB | 2013/02/13 12:00 | Winthrop v Charleston Southern | L | 70-65 |
| NCAAB | 2013/01/09 12:00 | Charleston Southern v Winthrop | W | 75-63 |
| NCAAB | 2012/01/21 12:00 | Charleston Southern v Winthrop | W | 77-66 |
| NCAAB | 2011/02/10 12:00 | Winthrop v Charleston Southern | L | 75-68 |
| NCAAB | 2011/01/15 12:00 | Charleston Southern v Winthrop | W | 69-60 |
| NCAAB | 2010/01/28 12:00 | Winthrop v Charleston Southern | L | 55-53 |
| NCAAB | 2010/01/04 12:00 | Charleston Southern v Winthrop | W | 57-54 |
| NCAAB | 2009/02/24 12:00 | Winthrop v Charleston Southern | L | 57-52 |
| NCAAB | 2008/02/26 12:00 | Winthrop v Charleston Southern | L | 63-49 |
| NCAAB | 2008/01/28 12:00 | Charleston Southern v Winthrop | L | 64-81 |
| NCAAB | 2007/02/27 12:00 | Winthrop v Charleston Southern | L | 72-42 |
| NCAAB | 2007/02/14 12:00 | Winthrop v Charleston Southern | L | 78-54 |
| NCAAB | 2007/01/08 12:00 | Charleston Southern v Winthrop | L | 52-75 |
| NCAAB | 2006/01/28 12:00 | Winthrop v Charleston Southern | L | 76-59 |
| NCAAB | 2006/01/16 12:00 | Charleston Southern v Winthrop | L | 61-79 |
| NCAAB | 2005/03/05 12:00 | Winthrop v Charleston Southern | L | 68-46 |
| NCAAB | 2005/02/26 12:00 | Charleston Southern v Winthrop | L | 62-65 |
| NCAAB | 2005/01/25 12:00 | Winthrop v Charleston Southern | L | 58-45 |
| NCAAB | 2004/02/21 12:00 | Charleston Southern v Winthrop | L | 48-72 |