| WTA - Barranquilla | 08/16 19:00 | 26 | Caroline Dolehide v Varvara Lepchenko | 3-6,4-6 | |
| WTA - Barranquilla | 08/14 21:10 | 25 | [108] Caroline Dolehide v Alana Smith [316] | 7-6,6-3 | |
| ITF - W100 Landisville | 08/11 19:10 | 27 | [108] Caroline Dolehide v Makenna Jones [283] | 6-7,6-4,4-6 | |
| ITF - W100 Landisville | 08/10 20:55 | 26 | [108] Caroline Dolehide v Elsa Jacquemot [186] | 6-4,6-4 | |
| ITF - W100 Landisville | 08/09 21:30 | 25 | [108] Caroline Dolehide v Marcela Zacarias [222] | 6-4,1-6,6-3 | |
| ITF - W60 Lexington | 08/06 16:45 | 29 | [105] Caroline Dolehide v Renata Zarazua [235] | 6-1,6-7,5-7 | |
| ITF - W60 Lexington | 08/05 19:55 | 28 | [105] Caroline Dolehide v Yafan Wang [175] | 7-6,6-4 | |
| ITF - W60 Lexington | 08/04 23:00 | 27 | [105] Caroline Dolehide v Makenna Jones [299] | 6-4,7-6 | |
| ITF - W60 Lexington | 08/03 19:00 | 26 | [105] Caroline Dolehide v Victoria Hu [418] | 6-4,6-1 | |
| ITF - W60 Lexington | 08/02 13:55 | 25 | [105] Caroline Dolehide v Dalayna Hewitt [500] | 4-6,7-6,6-1 | |
| Wimbledon - Feminino | 07/03 15:35 | 23 | [10] Daria Kasatkina v Caroline Dolehide [100] | 6-1,6-4 | |
| WTA - Eastbourne | 06/24 10:00 | 14 | [100] Caroline Dolehide v Madison Brengle [112] | 6-7,7-5,6-7 | |
| WTA - Birmingham | 06/17 14:50 | 14 | [186] Emina Bektas v Caroline Dolehide [99] | 6-3,7-5 | |
| WTA - Valência | 06/14 15:30 | 26 | [99] Caroline Dolehide v Tamara Korpatsch [124] | 1-6,3-6 | |
| WTA - Valência | 06/13 09:00 | 25 | [99] Caroline Dolehide v Elsa Jacquemot [189] | 6-2,6-2 | |
| WTA - La Bisbal d'Empordà | 06/09 16:15 | 27 | [114] Arantxa Rus v Caroline Dolehide [101] | 2-6,6-2,6-4 | |
| WTA - La Bisbal d'Empordà | 06/08 12:00 | 26 | [130] Marina Bassols Ribera v Caroline Dolehide [101] | 4-6,3-6 | |
| WTA - La Bisbal d'Empordà | 06/06 14:40 | 25 | [215] Ankita Raina v Caroline Dolehide [101] | 3-6,6-7 | |
| Open de França - Feminino | 05/23 15:50 | 14 | [99] Caroline Dolehide v Maria Carle [149] | 1-6,2-6 | |
| ITF - W60 Naples | 05/14 13:50 | 29 | [112] Caroline Dolehide v Yulia Starodubtsewa [499] | 7-5,7-5 | |
| ITF - W60 Naples | 05/13 13:45 | 28 | [112] Caroline Dolehide v Sophie Chang [280] | 6-2,7-5 | |
| ITF - W60 Naples | 05/12 15:45 | 27 | [112] Caroline Dolehide v Renata Zarazua [244] | 7-5,6-1 | |
| ITF - W60 Naples | 05/11 16:10 | 26 | Caroline Dolehide v Haley Giavara | 6-1,6-4 | |
| ITF - W60 Naples | 05/10 15:35 | 25 | [112] Caroline Dolehide v Yuki Naito [300] | 6-2,6-1 | |
| ITF - W100 Bonita Springs | 05/06 16:55 | 28 | [123] Caroline Dolehide v Kayla Day [183] | 6-7,6-1,0-6 | |
| ITF - W100 Bonita Springs | 05/05 16:40 | 27 | Kaitlin Quevedo v Caroline Dolehide | 0-6,0-6 | |
| ITF - W100 Bonita Springs | 05/04 19:00 | 26 | [239] Louisa Chirico v Caroline Dolehide [123] | 4-6,4-6 | |
| ITF - W100 Bonita Springs | 05/03 21:25 | 25 | Yulia Starodubtseva v Caroline Dolehide | 4-6,4-6 | |
| ITF - W60 Charlottesville | 04/29 17:25 | 28 | [155] Ashlyn Krueger v Caroline Dolehide [123] | 6-4,7-5 | |
| ITF - W60 Charlottesville | 04/28 17:30 | 27 | [265] Renata Zarazua v Caroline Dolehide [123] | 3-6,3-6 |