[193] Robin Montgomery 4-6,4-6 Madison Keys [21] 2023-03-24 18:35
Stadium: Grandstand Round: 24 Ground: Hardcourt outdoor
Home History
| WTA Miami | 2023/03/22 16:55 | Robin Montgomery v Ana Bogdan | 3-6,6-3,6-3 |
| WTA Indian Wells | 2023/03/06 19:00 | Robin Montgomery v Magdalena Frech | 6-7,3-6 |
| WTA Austin | 2023/03/01 00:55 | Robin Montgomery v Coco Vandeweghe | 2-6,7-6,6-7 |
| WTA Austin | 2023/02/26 16:30 | Robin Montgomery v Elvina Kalieva | 7-6,6-1 |
| WTA Austin | 2023/02/25 17:05 | Jodie Anna Burrage v Robin Montgomery | 4-6,5-7 |
| ITF W60 Orlando | 2023/02/07 18:30 | Robin Montgomery v Elizabeth Mandlik | 5-7,6-4,4-6 |
| ITF W60 Rome GA | 2023/02/02 16:00 | Robin Montgomery v Ashley Lahey | 3-6,6-1,3-6 |
| ITF W60 Rome GA | 2023/02/01 17:30 | Kayla Day v Robin Montgomery | 6-7,6-7 |
Away History
| WTA Dubai | 2023/02/23 13:10 | Madison Keys v Coco Gauff | 2-6,5-7 |
| WTA Dubai | 2023/02/22 09:55 | Madison Keys v Victoria Azarenka | 6-2,6-1 |
| WTA Dubai | 2023/02/21 08:00 | Caroline Garcia v Madison Keys | 5-7,4-6 |
| WTA Dubai | 2023/02/19 08:00 | Jasmine Paolini v Madison Keys | 1-6,1-6 |
| WTA Doha | 2023/02/14 12:30 | Madison Keys v Jelena Ostapenko | 5-7,2-6 |
| Australian Open Women | 2023/01/20 08:00 | Madison Keys v Victoria Azarenka | 6-1,2-6,1-6 |
| Australian Open Women | 2023/01/18 06:20 | Madison Keys v Xinyu Wang | 6-3,6-2 |
| Australian Open Women | 2023/01/16 10:20 | Madison Keys v Anna Blinkova | 6-4,3-6,6-2 |