Stadium: Center Court Round: 29 Ground: Hardcourt outdoor
| ITF Women Indian Harbour | 2018/04/11 17:30 | Ann Li v Caroline Dolehide | 4-6,5-7 |
| ITF W60 - Concord | 2019/08/16 15:00 | Olga Govortsova v Caroline Dolehide | 6-7,4-6 |
| ITF W60 - Concord | 2019/08/15 15:00 | Caroline Dolehide v Ana Bogdan | 6-4,6-3 |
| ITF W60 - Concord | 2019/08/14 16:00 | Lin Zhu v Caroline Dolehide | 1-6,1-6 |
| ITF W60 - Concord | 2019/08/13 18:40 | Nina Stojanovic v Caroline Dolehide | 1-6,6-3,6-7 |
| ITF W60 - Berkeley | 2019/07/19 19:10 | Caroline Dolehide v Sachia Vickery | 3-6,5-7 |
| ITF W60 - Berkeley | 2019/07/19 00:00 | Hailey Baptiste v Caroline Dolehide | 4-6,4-6 |
| ITF W60 - Berkeley | 2019/07/18 00:00 | Katie Volynets v Caroline Dolehide | 7-5,2-6,6-7 |
| ITF W60 - Honolulu | 2019/07/13 21:00 | Caroline Dolehide v Nicole Gibbs | 4-6,7-6,4-6 |
| ITF W60 - Concord | 2019/08/16 19:30 | Usue Maitane Arconada v Ann Li | 6-2,1-6,4-6 |
| ITF W60 - Concord | 2019/08/15 15:00 | Ann Li v Magdalena Frech | 6-3,6-2 |
| ITF W60 - Concord | 2019/08/14 17:45 | En Shuo Liang v Ann Li | 2-6,3-6 |
| ITF W60 - Concord | 2019/08/13 19:20 | Ann Li v Elizabeth Halbauer | 6-0,6-7,7-6 |
| ITF W60 - Lexington | 2019/08/04 17:00 | Dabin Kim v Ann Li | 6-1,6-3 |
| ITF W60 - Lexington | 2019/08/03 20:00 | Robin Anderson v Ann Li | 3-6,4-6 |
| ITF W60 - Lexington | 2019/08/02 15:00 | Jamie Loeb v Ann Li | 6-4,1-6,1-6 |
| ITF W60 - Lexington | 2019/08/01 16:00 | Peyton Stearns v Ann Li | 5-7,3-6 |