Round: 25 Ground: Hardcourt outdoor
| ITF W80 Macon | 2020/10/21 13:50 | Caroline Dolehide v Katie Volynets | 6-7,3-6 |
| French Open - nők | 2020/09/22 13:35 | Mayo Hibi v Caroline Dolehide | 3-6,7-5,7-5 |
| US Open - nők | 2020/08/31 17:10 | Caroline Dolehide v Anna-Lena Friedsam | 2-6,2-6 |
| WTA New York | 2020/08/21 15:00 | Laura Siegemund v Caroline Dolehide | 6-3,6-3 |
| WTA New York | 2020/08/20 16:35 | Caroline Dolehide v Jasmine Paolini | 6-3,2-6,6-4 |
| WTA Lexington | 2020/08/11 17:40 | Caroline Dolehide v Cori Gauff | 5-7,5-7 |
| WTA Lexington | 2020/08/10 14:00 | Jamie Loeb v Caroline Dolehide | 2-6,5-7 |
| WTA Lexington | 2020/08/09 14:00 | Kateryna Volodko v Caroline Dolehide | 3-6,6-4,2-6 |
| ITF W80 Macon | 2020/10/21 22:10 | Astra Sharma v Francesca Di Lorenzo | 3-6,4-6 |
| French Open - nők | 2020/09/30 09:30 | Astra Sharma v Ekaterina Alexandrova | 3-6,3-6 |
| French Open - nők | 2020/09/27 09:00 | Anna Blinkova v Astra Sharma | 3-6,6-2,5-7 |
| French Open - nők | 2020/09/25 09:50 | Astra Sharma v Martina Trevisan | 1-6,1-6 |
| French Open - nők | 2020/09/24 09:30 | Astra Sharma v Yuki Naito | 6-4,6-4 |
| French Open - nők | 2020/09/23 08:00 | Astra Sharma v Irina Ramialison | 6-4,6-4 |
| US Open - nők | 2020/08/31 22:55 | Astra Sharma v Dayana Yastremska | 3-6,7-6,6-7 |
| WTA New York | 2020/08/21 18:40 | Astra Sharma v Vera Zvonareva | 4-6,2-6 |