| ITF - W80 Tyler | 10/29 16:45 | 25 | [156] Sachia Vickery v Caroline Dolehide [148] | 1-6,3-6 | |
| ITF - W80 Macon | 10/22 14:00 | 25 | Caroline Dolehide v Astra Sharma | Cancelled | |
| ITF - W80 Macon | 10/21 13:50 | 25 | [148] Caroline Dolehide v Katie Volynets [325] | 6-7,3-6 | |
| Open de França - Feminino | 09/22 13:35 | 14 | [181] Mayo Hibi v Caroline Dolehide [140] | 3-6,7-5,7-5 | |
| Open dos EUA - Feminino | 08/31 17:10 | 23 | [135] Caroline Dolehide v Anna-Lena Friedsam [109] | 2-6,2-6 | |
| WTA - Nova Iorque | 08/21 15:00 | 19 | [67] Laura Siegemund v Caroline Dolehide [136] | 6-3,6-3 | |
| WTA - Nova Iorque | 08/20 16:35 | 44 | [136] Caroline Dolehide v Jasmine Paolini [96] | 6-3,2-6,6-4 | |
| WTA - Lexington | 08/11 17:40 | 25 | [134] Caroline Dolehide v Cori Gauff [53] | 5-7,5-7 | |
| WTA - Lexington | 08/10 14:00 | 168 | [277] Jamie Loeb v Caroline Dolehide [134] | 2-6,5-7 | |
| WTA - Lexington | 08/09 14:00 | 45 | [347] Kateryna Bondarenko v Caroline Dolehide [134] | 3-6,6-4,2-6 | |
| US Invitational - Feminino | 06/26 20:00 | 1 | [134] Caroline Dolehide v Amanda Anisimova [28] | 7-5,5-7,2-10 | |
| US Invitational - Feminino | 06/25 20:00 | 1 | [134] Caroline Dolehide v Madison Keys [13] | 1-6,7-6,4-10 | |
| Matchplay 120 - Feminino | 06/12 21:00 | - | Caroline Dolehide v Francesca Di Lorenzo | View | |
| Matchplay 120 - Feminino | 06/10 14:00 | - | [134] Caroline Dolehide v Jamie Loeb [277] | 4-6,6-2,6-4 | |
| Matchplay 120 - Feminino | 06/09 18:00 | 1 | [134] Caroline Dolehide v Whitney Osuigwe [143] | 6-4,6-4 | |
| Matchplay 120 - Feminino | 06/05 16:00 | 1 | [277] Jamie Loeb v Caroline Dolehide [134] | 6-4,1-6,7-5 | |
| Matchplay 120 - Feminino | 06/02 13:45 | - | [65] Laura Siegemund v Caroline Dolehide [134] | 0-0 | |
| Matchplay 120 - Feminino | 06/01 13:13 | - | [277] Jamie Loeb v Caroline Dolehide [134] | 5-7,0-0 | |
| Matchplay 120 - Feminino | 05/30 18:00 | - | [65] Laura Siegemund v Caroline Dolehide [134] | 3-6,4-6 | |
| Matchplay 120 - Feminino | 05/28 20:00 | 1 | [134] Caroline Dolehide v Jamie Loeb [277] | Interrupted | |
| WTA - Monterrey | 03/02 23:25 | 25 | [142] Olga Govortsova v Caroline Dolehide [131] | 3-6,6-2,6-1 | |
| WTA - Monterrey | 03/01 22:15 | 64 | [159] Lara Arruabarrena v Caroline Dolehide [131] | 6-4,7-6 | |
| WTA - Monterrey | 02/29 22:00 | 45 | [308] Ana Sofia Sanchez v Caroline Dolehide [139] | 3-6,6-4,5-7 | |
| WTA - Acapulco | 02/27 01:20 | 26 | [139] Caroline Dolehide v Christina McHale [86] | 7-5,4-6,3-6 | |
| WTA - Acapulco | 02/26 03:05 | 25 | [132] Usue Maitane Arconada v Caroline Dolehide [139] | 2-6,2-6 | |
| WTA - Acapulco | 02/23 22:00 | 64 | [153] Giulia G-Monticone v Caroline Dolehide [142] | 1-6,6-7 | |
| WTA - Acapulco | 02/22 22:00 | 45 | [150] Martina Trevisan v Caroline Dolehide [142] | 6-4,3-6,2-6 | |
| ITF - W100 Nicholasville | 02/12 23:55 | 25 | [289] Claire Liu v Caroline Dolehide [137] | 6-1,6-4 | |
| ITF - W100 Midland | 02/06 18:30 | 26 | [135] Caroline Dolehide v Irina Falconi [385] | 6-1,1-6,1-6 | |
| ITF - W100 Midland | 02/05 18:40 | 25 | [135] Caroline Dolehide v Grace Min [281] | 6-1,6-4 |