Stadium: Estadio Arena GNP Seguros (Acapulco, MEXICO) Round: 25 Ground: Hardcourt outdoor
| WTA Tianjin | 2019/10/12 04:45 | Veronika Kudermetova v Heather Watson | 1-6,4-6 |
| WTA Tianjin | 2019/10/11 07:40 | Magda Linette v Heather Watson | 5-7,7-6,6-7 |
| WTA Tianjin | 2019/10/10 06:05 | Heather Watson v Qiang Wang | 6-3,6-0 |
| WTA Tianjin | 2019/10/07 07:35 | Kateryna Volodko v Heather Watson | 4-6,6-7 |
| WTA Beijing | 2019/09/28 05:40 | Magda Linette v Heather Watson | 6-2,6-1 |
| WTA Beijing | 2019/09/27 03:00 | Heather Watson v Paula Badosa | 6-3,6-4 |
| WTA Wuhan | 2019/09/20 03:00 | Rebecca Peterson v Heather Watson | 6-2,6-2 |
| WTA New Haven | 2019/09/07 14:00 | Heather Watson v Usue Maitane Arconada | 3-6,7-5,0-6 |
| ITF W60 Templeton | 2019/09/29 20:00 | Shelby Rogers v Coco Vandeweghe | 4-6,6-2,6-3 |
| ITF W60 Templeton | 2019/09/28 22:00 | Grace Min v Coco Vandeweghe | 3-6,3-6 |
| ITF W60 Templeton | 2019/09/27 21:00 | Hanna Chang v Coco Vandeweghe | 3-6,6-2,3-6 |
| ITF W60 Templeton | 2019/09/26 20:45 | Giuliana Olmos v Coco Vandeweghe | 6-7,6-4,2-6 |
| ITF W60 Templeton | 2019/09/26 01:35 | Coco Vandeweghe v Usue Maitane Arconada | 6-4,6-4 |
| US Open Women | 2019/08/26 21:50 | Sofia Kenin v Coco Vandeweghe | 7-6,6-3 |
| WTA New York | 2019/08/19 18:50 | Coco Vandeweghe v Anna Blinkova | 3-6,0-6 |
| WTA Cincinnati | 2019/08/10 22:00 | Yafan Wang v Coco Vandeweghe | 6-2,6-2 |