| ITF - W60 Berkeley | 07/19 00:00 | 26 | [290] Hailey Baptiste v Caroline Dolehide [256] | 4-6,4-6 | |
| ITF - W60 Berkeley | 07/18 00:00 | 25 | [393] Katie Volynets v Caroline Dolehide [256] | 7-5,2-6,6-7 | |
| ITF - W60 Honolulu | 07/13 21:00 | 28 | [269] Caroline Dolehide v Nicole Gibbs [129] | 4-6,7-6,4-6 | |
| ITF - W60 Honolulu | 07/12 20:00 | 27 | [345] Kayla Day v Caroline Dolehide [269] | 7-5,3-6,1-6 | |
| ITF - W60 Honolulu | 07/11 21:50 | 26 | [482] Natasha Subhash v Caroline Dolehide [269] | 2-6,3-6 | |
| ITF - W60 Honolulu | 07/10 22:35 | 25 | [269] Caroline Dolehide v Ayano Shimizu [208] | 4-6,6-1,6-1 | |
| Wimbledon - Feminino | 06/26 14:20 | 45 | [268] Caroline Dolehide v Tereza Martincova [139] | 1-6,6-7 | |
| Wimbledon - Feminino | 06/25 10:30 | 44 | [205] Alexandra Cadantu v Caroline Dolehide [268] | 1-6,6-3,3-6 | |
| ITF - W100 Ilkley | 06/17 14:00 | 45 | [170] Veronica Cepede Royg v Caroline Dolehide [269] | 6-3,6-4 | |
| WTA - Nottingham | 06/09 12:20 | 45 | [196] Caroline Dolehide v Veronica Cepede Royg [171] | 4-6,3-6 | |
| ITF - W100 Surbiton | 06/06 12:25 | 26 | [54] Alison Van Uytvanck v Caroline Dolehide [196] | 6-4,3-6,6-4 | |
| ITF - W100 Surbiton | 06/05 13:05 | 25 | [196] Caroline Dolehide v Priscilla Hon [132] | 6-2,6-1 | |
| ITF - W100 Surbiton | 06/03 14:35 | 45 | [163] Danielle Lao v Caroline Dolehide [196] | 3-6,4-6 | |
| ITF - W100 Surbiton | 06/03 10:00 | 45 | [240] Jamie Loeb v Caroline Dolehide [196] | 4-6,3-6 | |
| ITF - W100 Bonita Springs | 05/07 21:55 | 25 | [152] Veronica Cepede Royg v Caroline Dolehide [201] | 6-1,6-4 | |
| ITF - W100 Charleston | 05/01 18:35 | 25 | [302] Louisa Chirico v Caroline Dolehide [207] | 6-0,6-4 | |
| ITF - W80 Charlottesville | 04/25 14:00 | 26 | [101] Taylor Townsend v Caroline Dolehide [210] | 6-2,6-3 | |
| ITF - W80 Charlottesville | 04/24 18:00 | 25 | [140] Ingrid Neel v Caroline Dolehide [210] | 1-6,6-3,0-6 | |
| ITF - W80 Dothan | 04/17 20:45 | 25 | [162] Lauren Davis v Caroline Dolehide [229] | 6-3,7-5 | |
| ITF - W25 Pelham | 04/14 18:00 | 29 | [156] Barbora Krejcikova v Caroline Dolehide [180] | 6-4,6-3 | |
| ITF - W25 Pelham | 04/13 17:30 | 28 | [191] Sesil Karatantcheva v Caroline Dolehide [180] | 3-6,6-7 | |
| ITF - W25 Pelham | 04/12 15:00 | 27 | [365] Sophie Chang v Caroline Dolehide [180] | 2-6,3-6 | |
| ITF - W25 Pelham | 04/11 15:00 | 26 | [304] Katarzyna Piter v Caroline Dolehide [180] | 3-6,1-6 | |
| ITF - W25 Pelham | 04/10 19:05 | 25 | [260] Urszula Radwanska v Caroline Dolehide [180] | 4-6,1-6 | |
| WTA - Charleston | 03/31 14:30 | 46 | [154] Caroline Dolehide v Nadiia Kichenok [41] | 6-7,6-4,6-7 | |
| WTA - Charleston | 03/30 16:00 | 45 | [154] Caroline Dolehide v Lidziya Marozava [42] | 6-2,6-3 | |
| WTA - Miami | 03/18 18:10 | 44 | [154] Caroline Dolehide v Magda Linette [88] | 5-7,6-7 | |
| WTA - Indian Wells | 03/04 23:15 | 44 | [109] Stefanie Voegele v Caroline Dolehide [141] | 6-2,3-6,6-3 | |
| WTA - Indian Wells | 02/25 21:05 | 24 | [116] Olga Danilovic v Caroline Dolehide [133] | 4-6,6-3,6-1 | |
| ITF - W25 Rancho Santa Fe | 02/20 18:00 | 25 | [131] Caroline Dolehide v Gabriela Ce [450] | 6-7,5-7 |