Stadium: Stadium 2 Round: 27 Ground: Hardcourt outdoor
| ITF W60 Lexington | 2023/08/03 19:00 | Caroline Dolehide v Victoria Hu | 6-4,6-1 |
| ITF W60 Lexington | 2023/08/02 13:55 | Caroline Dolehide v Dalayna Hewitt | 4-6,7-6,6-1 |
| Wimbledon Women | 2023/07/03 15:35 | Daria Kasatkina v Caroline Dolehide | 6-1,6-4 |
| WTA Eastbourne | 2023/06/24 10:00 | Caroline Dolehide v Brengle, Madison | 6-7,7-5,6-7 |
| WTA Birmingham | 2023/06/17 14:50 | Emina Bektas v Caroline Dolehide | 6-3,7-5 |
| WTA Valencia | 2023/06/14 15:30 | Caroline Dolehide v Tamara Korpatsch | 1-6,3-6 |
| WTA Valencia | 2023/06/13 09:00 | Caroline Dolehide v Elsa Jacquemot | 6-2,6-2 |
| WTA La Bisbal D'Emporda | 2023/06/09 16:15 | Arantxa Rus v Caroline Dolehide | 2-6,6-2,6-4 |
| ITF W60 Lexington | 2023/08/03 22:20 | Jones, Makenna v Katie Swan | 6-2,6-3 |
| ITF W60 Lexington | 2023/08/03 00:50 | Elizabeth Eades v Jones, Makenna | 0-6,1-6 |
| ITF W60 Dallas | 2023/07/28 15:55 | Jones, Makenna v Yafan Wang | 4-6,1-6 |
| ITF W60 Dallas | 2023/07/27 14:55 | Hanna Chang v Jones, Makenna | 3-6,4-6 |
| ITF W60 Dallas | 2023/07/26 17:40 | Jones, Makenna v Brantmeier, Reese | 6-4,6-0 |
| ITF W100 Granby | 2023/07/20 13:55 | Emina Bektas v Jones, Makenna | 7-6,6-4 |
| ITF W100 Granby | 2023/07/19 13:55 | Jones, Makenna v Kupres, Mia | 7-6,0-6,6-3 |
| ITF W40 Palma del Rio | 2023/06/29 18:30 | Garcia Perez, Georgina v Jones, Makenna | 4-6,2-6 |