Stadium: Court 2 Round: 25 Ground: Hardcourt indoor
| ITF - W25 Cherbourg | 2020/10/14 09:00 | Robin Montgomery v Robin Anderson | 3-6,7-5,6-3 |
| ITF - W25 Cherbourg | 2020/10/16 09:00 | Harriet Dart v Robin Montgomery | 6-2,6-4 |
| ITF - W25 Cherbourg | 2020/10/15 13:00 | Robin Montgomery v Valeria Savinykh | 6-1,6-1 |
| ITF - W25 Cherbourg | 2020/10/14 09:00 | Robin Montgomery v Robin Anderson | 3-6,7-5,6-3 |
| US Open - Feminin | 2020/09/01 01:20 | Robin Montgomery v Yulia Putintseva | 1-6,3-6 |
| WTA - New York | 2020/08/20 21:00 | Sorana Cirstea v Robin Montgomery | 6-1,6-4 |
| ITF - W25 Las Vegas | 2020/03/08 18:00 | Xiaodi You v Robin Montgomery | 6-2,3-6,4-6 |
| ITF - W25 Las Vegas | 2020/03/07 20:30 | Katherine Sebov v Robin Montgomery | 5-7,6-3,1-6 |
| ITF - W25 Las Vegas | 2020/03/06 21:00 | Robin Montgomery v Emiliana Arango | 6-3,6-2 |
| ITF - W25 Cherbourg | 2020/10/14 09:00 | Robin Montgomery v Robin Anderson | 3-6,7-5,6-3 |
| French Open - Feminin | 2020/09/22 14:05 | Robin Anderson v Xinyu Wang | 4-6,2-6 |
| WTA - Praga | 2020/09/02 12:05 | Valentini Grammatikopoulou v Robin Anderson | 3-6,6-4,6-3 |
| WTA - Praga | 2020/09/01 08:00 | Robin Anderson v Martina Di Giuseppe | 6-4,6-3 |
| WTA - Praga | 2020/08/30 15:00 | Robin Anderson v Dejana Radanovic | 7-6,6-4 |
| WTA - Lexington | 2020/08/10 19:15 | Robin Anderson v Bethanie Mattek-Sands | 3-6,6-4,5-7 |
| WTA - Lexington | 2020/08/09 21:00 | Ann Li v Robin Anderson | 6-7,5-7 |
| ITF - W25 Las Vegas | 2020/03/04 18:00 | Emiliana Arango v Robin Anderson | 6-2,5-7,6-2 |