| US Open - Damer | 08/26 23:00 | 15 | [188] Caroline Dolehide v Victoria Duval [457] | 5-7,6-4,6-3 | |
| US Open - Damer | 08/25 22:15 | 14 | [118] Irina Maria Bara v Caroline Dolehide [188] | 4-6,1-6 | |
| WTA Chicago | 08/17 17:35 | 25 | [171] Caroline Dolehide v Storm Sanders [139] | 3-6,6-4,2-6 | |
| WTA Chicago | 08/16 16:00 | 19 | [159] Lesley P Kerkhove v Caroline Dolehide [171] | 6-2,2-6,3-6 | |
| WTA Chicago | 08/16 16:00 | 14 | Harmony Tan v Caroline Dolehide | Cancelled | |
| ITF W100 - Landisville | 08/11 15:45 | 25 | [171] Caroline Dolehide v Mayo Hibi [215] | 4-6,4-6 | |
| WTA Concord | 08/05 20:50 | 26 | [171] Caroline Dolehide v Katrina Scott [372] | 6-1,0-6,5-7 | |
| WTA Concord | 08/03 14:00 | 25 | [171] Caroline Dolehide v Robin Anderson [218] | 6-3,6-4 | |
| Wimbledon - Damer | 06/22 18:10 | 14 | [118] Kristie Ahn v Caroline Dolehide [163] | 1-6,7-5,6-2 | |
| WTA Nottingham | 06/08 14:40 | 25 | [164] Caroline Dolehide v Tereza Martincova [94] | 2-6,3-6 | |
| WTA Nottingham | 06/07 10:00 | 24 | [164] Caroline Dolehide v Giulia Gatto Monticone [172] | 6-4,6-3 | |
| Franska öppna - Damer | 05/25 17:05 | 14 | [116] Tsvetana Pironkova v Caroline Dolehide [164] | 6-7,6-2,6-4 | |
| ITF W100 - Bonita Springs | 05/12 15:35 | 25 | [159] Francesca Di Lorenzo v Caroline Dolehide [162] | 6-2,6-7,7-6 | |
| ITF W100 - Charleston | 05/05 16:55 | 25 | [161] Caroline Dolehide v Aldila Sutjiadi [401] | 1-6,6-2,4-6 | |
| WTA Charleston Kval | 04/10 16:15 | 14 | [217] Grace Min v Caroline Dolehide [155] | 7-6,2-6,7-5 | |
| WTA Charleston | 04/06 17:25 | 24 | [155] Caroline Dolehide v Hailey Baptiste [216] | 3-6,3-6 | |
| WTA Charleston | 04/04 16:35 | 19 | [157] Caroline Dolehide v Storm Sanders [203] | 6-2,4-6,6-7 | |
| WTA Charleston | 04/03 15:40 | 14 | [157] Caroline Dolehide v Mirjam Bjorklund [313] | 6-4,6-3 | |
| WTA Miami | 03/22 21:40 | 14 | [108] Timea Babos v Caroline Dolehide [157] | 4-6,6-2,6-2 | |
| WTA Monterrey | 03/15 21:10 | 25 | [155] Caroline Dolehide v Viktoria Kuzmova [104] | 3-6,1-6 | |
| WTA Guadalajara | 03/10 01:00 | 25 | [144] Eugenie Bouchard v Caroline Dolehide [154] | 3-6,6-1,6-3 | |
| WTA Guadalajara | 03/07 20:00 | 19 | [138] Olga Govortsova v Caroline Dolehide [154] | 6-7,7-5,6-7 | |
| WTA Guadalajara | 03/06 22:00 | 14 | [229] Ellen Perez v Caroline Dolehide [154] | 3-6,7-5,4-6 | |
| ITF W25 - Boca Raton | 02/25 15:50 | 26 | [186] Maria C O Serrano v Caroline Dolehide [154] | 6-3,7-6 | |
| ITF W25 - Boca Raton | 02/24 15:00 | 25 | [283] Andrea Lazaro Garcia v Caroline Dolehide [154] | 7-6,3-6,2-6 | |
| WTA Yarra Valley Classic | 02/02 04:00 | 25 | [156] Vera Zvonareva v Caroline Dolehide [152] | 6-2,6-4 | |
| Australian Open - Damer | 01/10 10:20 | 60 | [151] Caroline Dolehide v Ellen Perez [235] | 3-6,7-5,5-7 | |
| ITF W100 - Charleston | 11/05 14:55 | 26 | [164] Maiar S A Abdelaziz v Caroline Dolehide [149] | 7-5,7-6 | |
| ITF W100 - Charleston | 11/04 18:40 | 25 | [149] Caroline Dolehide v Kristie Ahn [107] | 6-1,6-0 | |
| ITF W80 - Tyler | 10/30 17:00 | 26 | [148] Caroline Dolehide v Aliona Bolsova Zadoinov [101] | 6-7,6-4,3-6 |