| ITF - W100 Charleston | 04/28 19:50 | 26 | [173] Caroline Dolehide v Xiyu Wang [123] | 6-3,4-6,1-6 | |
| ITF - W100 Charleston | 04/27 16:25 | 25 | [173] Caroline Dolehide v Alycia Parks [163] | 7-5,7-5 | |
| ITF - W60 Charlottesville | 04/20 19:05 | 25 | [201] Seone Mendez v Caroline Dolehide [172] | 6-4,4-6,6-4 | |
| ITF - W100 Palm Harbor | 04/13 19:55 | 25 | [175] Caroline Dolehide v Alycia Parks [153] | 4-6,1-6 | |
| WTA - Charleston | 04/02 15:55 | 14 | [174] Caroline Dolehide v Louisa Chirico [300] | 3-6,6-3,3-6 | |
| WTA - Miami | 03/22 19:10 | 19 | [84] Anna Kalinskaya v Caroline Dolehide [174] | 7-5,6-4 | |
| WTA - Miami | 03/21 21:20 | 14 | [174] Caroline Dolehide v Dayana Yastremska [104] | Retired | |
| ITF - W60 Arcadia | 03/04 21:35 | 27 | [111] Chloe Paquet v Caroline Dolehide [178] | 6-2,6-3 | |
| ITF - W60 Arcadia | 03/03 18:00 | 26 | [192] Emina Bektas v Caroline Dolehide [178] | 7-6,3-6,2-6 | |
| ITF - W60 Arcadia | 03/02 18:00 | 25 | Caroline Dolehide v Robin Anderson | 6-4,6-4 | |
| WTA - Guadalajara | 02/25 01:00 | 26 | Daria Saville v Caroline Dolehide | 6-1,6-3 | |
| WTA - Guadalajara | 02/23 00:15 | 25 | [180] Caroline Dolehide v Lin Zhu [109] | 4-6,6-3,6-4 | |
| WTA - Guadalajara | 02/20 17:00 | 19 | [110] Dalma Galfi v Caroline Dolehide [181] | 6-7,4-6 | |
| WTA - Guadalajara | 02/19 17:00 | 14 | Caroline Dolehide v Nao Hibino | 6-0,6-4 | |
| ITF - W60 Rome, GA | 02/05 17:50 | 28 | [191] Caroline Dolehide v Alycia Parks [199] | 3-6,6-7 | |
| ITF - W60 Rome, GA | 02/04 16:00 | 27 | Katarina Jokic v Caroline Dolehide | 6-2,0-6,1-6 | |
| ITF - W60 Rome, GA | 02/03 16:50 | 26 | [149] Christina McHale v Caroline Dolehide [191] | 3-6,6-3,3-6 | |
| ITF - W60 Rome, GA | 02/02 18:00 | 25 | [191] Caroline Dolehide v Coco Vandeweghe [170] | Retired | |
| Open da Austrália - Feminino | 01/18 08:20 | 23 | [200] Caroline Dolehide v Danielle Collins [30] | 1-6,3-6 | |
| Open da Austrália - Feminino | 01/14 01:45 | 19 | [188] Julia Grabher v Caroline Dolehide [200] | 6-7,2-6 | |
| Open da Austrália - Feminino | 01/12 01:00 | 15 | [200] Caroline Dolehide v Xiaodi You [249] | 6-3,6-2 | |
| Open da Austrália - Feminino | 01/10 04:40 | 14 | [187] Yuliya Hatouka v Caroline Dolehide [200] | 4-6,2-6 | |
| ITF - W80 Macon | 10/21 15:30 | 26 | [272] Catherine Harrison v Caroline Dolehide [190] | 7-5,6-1 | |
| ITF - W80 Macon | 10/20 14:00 | 25 | [179] Kurumi Nara v Caroline Dolehide [190] | 6-7,4-6 | |
| ITF - W60 Rancho Santa Fe | 10/12 19:40 | 25 | [201] Caroline Dolehide v Fiona Ferro [83] | 2-6,7-5,2-6 | |
| WTA - Indian Wells | 10/05 23:50 | 19 | [224] En Shuo Liang v Caroline Dolehide [201] | 6-4,6-7,6-3 | |
| WTA - Indian Wells | 10/04 23:15 | 14 | [201] Caroline Dolehide v Grace Min [169] | 7-5,6-1 | |
| WTA - Chicago | 09/27 16:45 | 24 | [130] Maddison Inglis v Caroline Dolehide [181] | 4-6,6-2,6-4 | |
| WTA - Columbus | 09/19 22:10 | 25 | [183] Caroline Dolehide v Renata Zarazua [120] | 4-6,6-1,6-7 | |
| Open dos EUA - Feminino | 08/27 23:30 | 19 | [188] Caroline Dolehide v Olga Danilovic [145] | 4-6,6-0,2-6 |