| WTA - Colina | 11/11 19:00 | 27 | [84] Julia Grabher v Caroline Dolehide [172] | 2-6,1-6 | |
| WTA - Colina | 11/09 19:40 | 26 | [377] Emiliana Arango v Caroline Dolehide [172] | 4-6,4-6 | |
| WTA - Colina | 11/08 15:00 | 25 | [172] Caroline Dolehide v Su Jeong Jang [115] | 6-2,6-2 | |
| ITF - W80 Tyler | 10/26 21:00 | 25 | [172] Maria Lourdes Carle v Caroline Dolehide [160] | 0-6,6-2,7-5 | |
| WTA - Guadalajara | 10/18 17:20 | 24 | [16] Danielle Collins v Caroline Dolehide [175] | 6-4,6-1 | |
| WTA - Guadalajara | 10/16 20:45 | 19 | [181] Caroline Dolehide v Carolina Alves [175] | 6-4,6-2 | |
| WTA - Guadalajara | 10/15 20:50 | 14 | [121] Alycia Parks v Caroline Dolehide [181] | 4-6,6-3,4-6 | |
| WTA - San Diego | 10/11 19:45 | 25 | [22] Karolina Pliskova v Caroline Dolehide [181] | 6-3,6-4 | |
| WTA - San Diego | 10/09 17:00 | 19 | [36] Jil Teichmann v Caroline Dolehide [177] | 4-6,2-6 | |
| WTA - San Diego | 10/08 18:25 | 14 | [177] Caroline Dolehide v Madison Brengle [48] | 7-6,7-5 | |
| ITF - W80 Rancho Santa Fe | 10/04 20:05 | 25 | [219] Elvina Kalieva v Caroline Dolehide [177] | 6-4,7-5 | |
| ITF - W60 Templeton | 09/28 01:00 | 25 | [186] Katrina Scott v Caroline Dolehide [160] | 6-7,7-6,7-5 | |
| Open dos EUA - Feminino | 08/24 18:55 | 14 | [155] Caroline Dolehide v Mirjam Bjorklund [128] | 3-6,7-5,3-6 | |
| ITF - W100 Landisville | 08/13 14:00 | 26 | Su Jeong Jang v Caroline Dolehide | Cancelled | |
| ITF - W100 Landisville | 08/12 14:00 | 27 | [144] Caroline Dolehide v Na-Lae Han [247] | 4-6,6-7 | |
| ITF - W100 Landisville | 08/11 16:05 | 26 | Hibah Shaikh v Caroline Dolehide | 4-6,3-6 | |
| ITF - W100 Landisville | 08/10 21:30 | 25 | [461] Hiroko Kuwata v Caroline Dolehide [144] | 1-6,7-5,5-7 | |
| WTA - San Jose | 08/04 20:00 | 26 | [168] Caroline Dolehide v Aryna Sabalenka [6] | 7-5,1-6,5-7 | |
| WTA - San Jose | 08/02 17:00 | 25 | [230] Kayla Day v Caroline Dolehide [168] | 6-7,4-6 | |
| WTA - San Jose | 07/31 17:00 | 19 | [280] Storm Sanders v Caroline Dolehide [166] | 6-4,6-1 | |
| WTA - San Jose | 07/30 17:00 | 14 | [258] Francesca Di Lorenzo v Caroline Dolehide [166] | 3-6,4-6 | |
| ITF - W60 Evansville | 07/21 15:30 | 25 | [162] Caroline Dolehide v Ashlyn Krueger [314] | 4-6,4-6 | |
| ITF - W100 Charleston | 06/30 19:45 | 26 | [173] Caroline Dolehide v Elizabeth Mandlik [323] | 6-4,3-6,3-6 | |
| ITF - W100 Charleston | 06/29 13:00 | 25 | [173] Caroline Dolehide v Elizabeth Halbauer [400] | 6-2,3-6,6-4 | |
| ITF - W100 Ilkley | 06/15 10:00 | 25 | [98] Dalma Galfi v Caroline Dolehide [176] | 6-3,6-4 | |
| WTA - Nottingham | 06/04 10:00 | 14 | [258] Jana Fett v Caroline Dolehide [171] | 6-2,6-4 | |
| Open de França - Feminino | 05/18 12:45 | 15 | [223] Seone Mendez v Caroline Dolehide [173] | 7-6,7-5 | |
| Open de França - Feminino | 05/16 16:35 | 14 | [173] Caroline Dolehide v Elina Avanesyan [138] | 7-6,4-6,7-5 | |
| ITF - W100 Bonita Springs | 05/05 16:15 | 26 | [121] Katie Volynets v Caroline Dolehide [173] | 6-2,1-6,7-6 | |
| ITF - W100 Bonita Springs | 05/03 17:55 | 25 | [260] Allie Kiick v Caroline Dolehide [173] | 2-6,6-4,1-6 |