Stadium: Court 9 Round: 25 Ground: Hardcourt outdoor
| ITF W60 Berkeley | 2019/07/18 00:00 | Katie Volynets v Caroline Dolehide | 7-5,2-6,6-7 |
| French Open Women | 2020/09/22 13:35 | Hibi, Mayo 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 |
| New York, USA | 2020/08/21 15:00 | Laura Siegemund v Caroline Dolehide | 6-3,6-3 |
| New York, USA | 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 Gauff, Cori | 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 |
| US Invitational Women | 2020/06/26 20:00 | Caroline Dolehide v Amanda Anisimova | 7-5,5-7,2-10 |
| ITF W80 Macon | 2020/10/19 20:10 | Katie Volynets v Kyoka Okamura | 7-6,4-6,10-7 |
| ITF W25 Prerov | 2020/09/22 08:00 | Katie Volynets v Nika Radisic | 2-6,6-7 |
| ITF W25 Prerov | 2020/09/21 08:00 | Katie Volynets v Dohnalova, Rozalie | 6-3,6-1 |
| ITF W25 Frydek Mistek | 2020/09/17 08:00 | Katie Volynets v Qinwen Zheng | 1-6,1-6 |
| ITF W25 Prague | 2020/09/10 11:00 | Katie Volynets v Jesika Maleckova | 2-6,1-6 |
| ITF W25 Prague | 2020/09/09 11:20 | Mariam Bolkvadze v Katie Volynets | 3-6,0-6 |
| ITF W25 Prague | 2020/09/08 09:30 | Katie Volynets v Oana Georgeta Simion | 5-7,6-4,10-8 |
| ITF W25 Prague | 2020/09/07 10:30 | Katie Volynets v Mina Hodzic | 6-2,6-1 |