| ITF W25 Rancho Santa Fe | 02/20 18:00 | 25 | [131] Caroline Dolehide v Gabriela Ce [450] | 6-7,5-7 | |
| ITF W25 Rancho Santa Fe | 02/19 18:00 | 45 | Caroline Dolehide v Haley Giavara | 6-1,6-2 | |
| ITF W25 Rancho Santa Fe | 02/18 21:00 | 45 | Caroline Dolehide v Sabastiani Leon | 6-2,6-2 | |
| WTA Hua Hin | 01/26 07:35 | 45 | [129] Caroline Dolehide v Zhaoxuan Yang [24] | 6-7,6-2,5-7 | |
| Australian Open - ženy | 01/09 23:00 | 45 | [169] Danielle Lao v Caroline Dolehide [130] | 6-1,2-6,6-1 | |
| Australian Open - ženy | 01/08 02:55 | 44 | [216] Rebecca Marino v Caroline Dolehide [130] | 2-6,2-6 | |
| WTA Brisbane | 12/28 06:00 | 45 | [149] Harriet Dart v Caroline Dolehide [126] | 6-0,6-2 | |
| WTA Hongkong | 10/09 11:15 | 25 | [131] Caroline Dolehide v Ana Bogdan [78] | 7-6,3-6,5-7 | |
| WTA Hongkong | 10/07 03:35 | 64 | [133] Caroline Dolehide v Lesley Kerkhove [226] | 6-7,6-4,3-6 | |
| WTA Hongkong | 10/06 07:00 | 45 | Caroline Dolehide v Ho Ching Wu | 6-2,6-4 | |
| WTA Peking | 09/28 03:00 | 45 | [133] Caroline Dolehide v Lara Arruabarrena [76] | 6-4,4-6,4-6 | |
| WTA Wuhan | 09/21 05:10 | 45 | [138] Caroline Dolehide v Marketa Vondrousova [69] | 6-3,1-6,1-6 | |
| US Open - ženy | 08/27 23:40 | 23 | [119] Caroline Dolehide v Carina Witthoeft [101] | 3-6,6-7 | |
| WTA Cincinnati Qual | 08/11 21:10 | 44 | [124] Caroline Dolehide v Viktoria Kuzmova [57] | 4-6,4-6 | |
| WTA Montreal | 08/06 19:30 | 24 | [124] Caroline Dolehide v Venus Williams [14] | 5-7,1-6 | |
| WTA Montreal Qual | 08/05 19:00 | 45 | [66] Monica Puig v Caroline Dolehide [113] | 3-6,6-4,3-6 | |
| WTA Montreal Qual | 08/04 22:45 | 44 | [113] Caroline Dolehide v Yanina Wickmayer [94] | 6-3,6-4 | |
| WTA Washington | 07/31 18:00 | 25 | [113] Caroline Dolehide v Donna Vekic [44] | 3-6,4-6 | |
| ITF Women Ashland | 07/27 16:40 | 27 | Caroline Dolehide v Misaki Doi | Walkover | |
| ITF Women Ashland | 07/26 15:40 | 26 | [116] Caroline Dolehide v Francoise Abanda [195] | 6-7,6-3,6-3 | |
| ITF Women Ashland | 07/24 21:45 | 25 | [116] Caroline Dolehide v Victoria Duval [215] | 2-6,6-2,6-1 | |
| Wimbledon - ženy | 07/03 10:30 | 23 | [25] Daria Gavrilova v Caroline Dolehide [109] | 6-2,6-3 | |
| Wimbledon Women Qual | 06/28 13:15 | 46 | [113] Caroline Dolehide v Vera Zvonareva [141] | 2-6,3-6 | |
| Wimbledon Women Qual | 06/27 10:00 | 45 | [113] Caroline Dolehide v Jessica Pieri [214] | 6-2,6-3 | |
| Wimbledon Women Qual | 06/26 10:00 | 44 | [113] Caroline Dolehide v Miyu Kato [165] | 6-0,7-6 | |
| WTA Birmingham Qual | 06/16 10:00 | 45 | [106] Caroline Dolehide v Eugenie Bouchard [194] | 5-7,4-6 | |
| French Open - ženy | 05/30 12:35 | 24 | [13] Madison Keys v Caroline Dolehide [125] | 6-4,6-1 | |
| French Open - ženy | 05/28 09:00 | 23 | [126] Caroline Dolehide v Viktorija Golubic [110] | 6-4,6-4 | |
| French Open Women Qual | 05/25 10:00 | 46 | [161] Irina Bara v Caroline Dolehide [126] | 4-6,3-6 | |
| French Open Women Qual | 05/24 08:00 | 45 | [171] Marie Bouzková v Caroline Dolehide [126] | 6-4,3-6,5-7 |