Estadio: Stadium Round: 27 Ground: Hardcourt outdoor
| ITF W60 Lexington | 2023/08/04 23:00 | Caroline Dolehide v Makenna Jones | 6-4,7-6 |
| ITF W100 Landisville | 2023/08/10 20:55 | Caroline Dolehide v Elsa Jacquemot | 6-4,6-4 |
| ITF W100 Landisville | 2023/08/09 21:30 | Caroline Dolehide v Marcela Zacarias | 6-4,1-6,6-3 |
| ITF W60 Lexington | 2023/08/06 16:45 | Caroline Dolehide v Renata Zarazua | 6-1,6-7,5-7 |
| ITF W60 Lexington | 2023/08/05 19:55 | Caroline Dolehide v Yafan Wang | 7-6,6-4 |
| ITF W60 Lexington | 2023/08/04 23:00 | Caroline Dolehide v Makenna Jones | 6-4,7-6 |
| 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 - Femenino | 2023/07/03 15:35 | Daria Kasatkina v Caroline Dolehide | 6-1,6-4 |
| ITF W100 Landisville | 2023/08/10 20:15 | Makenna Jones v Olivia Gadecki | 6-4,6-2 |
| ITF W100 Landisville | 2023/08/09 23:10 | Makenna Jones v Astra Sharma | 3-6,7-5,6-3 |
| ITF W60 Lexington | 2023/08/04 23:00 | Caroline Dolehide v Makenna Jones | 6-4,7-6 |
| ITF W60 Lexington | 2023/08/03 22:20 | Makenna Jones v Katie Swan | 6-2,6-3 |
| ITF W60 Lexington | 2023/08/03 00:50 | Elizabeth Eades v Makenna Jones | 0-6,1-6 |
| ITF W60 Dallas | 2023/07/28 15:55 | Makenna Jones v Yafan Wang | 4-6,1-6 |
| ITF W60 Dallas | 2023/07/27 14:55 | Hanna Chang v Makenna Jones | 3-6,4-6 |
| ITF W60 Dallas | 2023/07/26 17:40 | Makenna Jones v Reese Brantmeier | 6-4,6-0 |