Stadium: Court 9 Round: 25 Ground: Clay
| ITF Women Sacramento | 2017/07/27 19:00 | Caroline Dolehide v Kristie Ahn | 1-6,6-7 |
| ITF W80 Tyler | 2020/10/30 17:00 | Caroline Dolehide v Aliona Bolsova Zadoinov | 6-7,6-4,3-6 |
| ITF W80 Tyler | 2020/10/29 16:45 | Sachia Vickery v Caroline Dolehide | 1-6,3-6 |
| ITF W80 Macon | 2020/10/21 13:50 | Caroline Dolehide v Katie Volynets | 6-7,3-6 |
| French Open Women | 2020/09/22 13:35 | Mayo Hibi v Caroline Dolehide | 3-6,7-5,7-5 |
| US Open Women | 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 |
| ITF W80 Tyler | 2020/10/29 16:55 | Hailey Baptiste v Kristie Ahn | 6-2,6-2 |
| ITF W80 Macon | 2020/10/22 16:20 | Sara Errani v Kristie Ahn | 6-3,6-4 |
| ITF W80 Macon | 2020/10/21 22:05 | Tessah Andrianjafitrimo v Kristie Ahn | 3-6,3-6 |
| French Open Women | 2020/09/28 13:05 | Kristie Ahn v Serena Williams | 6-7,0-6 |
| US Open Women | 2020/09/01 21:05 | Kristie Ahn v Serena Williams | 5-7,3-6 |
| WTA New York | 2020/08/21 16:50 | Leylah Annie Fernandez v Kristie Ahn | 6-4,6-1 |
| WTA New York | 2020/08/20 17:25 | Anna-Lena Friedsam v Kristie Ahn | 5-7,0-6 |
| WTA Lexington | 2020/08/10 14:00 | Kristie Ahn v Jovana Jovic | 2-6,6-4,6-2 |