[361] Robin Montgomery 3-6,3-6 Kaia Kanepi [63] 2021-12-20 15:00
Stadium: Stadium 1 Round: 23 Ground: Hardcourt outdoor
Home History
| WTA Limoges | 2021/12/14 18:05 | Robin Montgomery v Polona Hercog | 6-4,4-6,4-6 |
| US Open Women | 2021/08/25 18:05 | Robin Montgomery v Jodie Anna Burrage | 4-6,1-6 |
| WTA San Jose | 2021/08/01 22:05 | Ana Konjuh v Robin Montgomery | 6-3,7-6 |
| WTA San Jose | 2021/07/31 22:20 | Robin Montgomery v Arina Rodionova | 6-4,6-0 |
| ITF W25 Evansville | 2021/07/15 14:00 | Robin Montgomery v Catherine Harrison | 3-6,6-7 |
| ITF W25 Evansville | 2021/07/14 16:40 | Victoria Rodriguez v Robin Montgomery | 6-2,2-6,2-6 |
| ITF W100 Bonita Springs | 2021/05/12 19:00 | Madison Brengle v Robin Montgomery | 6-2,6-2 |
| WTA Miami | 2021/03/23 15:00 | Magda Linette v Robin Montgomery | 6-1,3-6,6-0 |
Away History
| ITF W25 Haabneeme | 2021/11/03 14:10 | Kaia Kanepi v Caijsa W Hennemann | 6-1,6-1 |
| WTA Indian Wells | 2021/10/07 01:05 | Kaia Kanepi v Madison Keys | 0-6,5-7 |
| WTA Chicago | 2021/09/28 14:00 | Jil Teichmann v Kaia Kanepi | 7-6,7-5 |
| ITF W25 Fort Worth | 2021/09/26 14:30 | Kaia Kanepi v Kayla Day | 6-2,6-1 |
| ITF W25 Fort Worth | 2021/09/25 14:30 | Kaia Kanepi v Alexandra Bozovic | 3-6,6-3,6-4 |
| ITF W25 Fort Worth | 2021/09/24 14:30 | Kaia Kanepi v Emma Navarro | 6-2,6-2 |
| ITF W25 Fort Worth | 2021/09/23 15:10 | Kaia Kanepi v Quinn Gleason | 6-3,6-2 |
| ITF W25 Fort Worth | 2021/09/21 18:10 | Kaia Kanepi v Sophie Chang | 6-1,5-7,6-1 |