[73] Sloane Stephens 6-7,7-5,6-1 Heather Watson [57] 2021-10-06 19:50
Stadium: Stadium 1 Round: 23 Ground: Hardcourt outdoor
Home History
| WTA - Chicago | 2021/09/28 16:00 | Sloane Stephens v Tamara Zidansek | 2-6,1-6 |
| US Open - Dames | 2021/09/03 20:00 | Angelique Kerber v Sloane Stephens | 5-7,6-2,6-3 |
| US Open - Dames | 2021/09/01 23:00 | Sloane Stephens v Cori Gauff | 6-4,6-2 |
| US Open - Dames | 2021/08/30 16:00 | Madison Keys v Sloane Stephens | 3-6,6-1,6-7 |
| WTA - Cincinnati | 2021/08/18 03:30 | Caroline Garcia v Sloane Stephens | 7-6,4-6,6-4 |
| WTA - Montreal | 2021/08/11 17:30 | Aryna Sabalenka v Sloane Stephens | 7-6,4-6,6-4 |
| WTA - Montreal | 2021/08/10 15:00 | Dayana Yastremska v Sloane Stephens | 4-6,6-1,4-6 |
| WTA - San Jose | 2021/08/06 02:00 | Danielle Rose Collins v Sloane Stephens | 3-6,6-4,6-3 |
Away History
| WTA Portoroz | 2021/09/13 16:35 | Heather Watson v Sorana Cirstea | 1-6,3-6 |
| US Open - Dames | 2021/08/30 18:50 | Heather Watson v Kaja Juvan | 1-6,4-6 |
| WTA - Cincinnati | 2021/08/18 18:00 | Ashleigh Barty v Heather Watson | 6-4,7-6 |
| WTA - Cincinnati | 2021/08/16 19:55 | Aliaksandra Sasnovich v Heather Watson | 2-6,6-3,1-6 |
| WTA - Cincinnati | 2021/08/15 17:30 | Rebecca Peterson v Heather Watson | 4-6,6-4,3-6 |
| WTA - Cincinnati | 2021/08/14 18:15 | Katie Volynets v Heather Watson | 7-5,2-6,2-6 |
| WTA - Montreal | 2021/08/08 18:00 | Heather Watson v Clara Burel | 6-1,4-6,4-6 |
| WTA - Montreal | 2021/08/07 18:10 | Heather Watson v Katherine Sebov | 6-0,6-3 |