| Australian Open - Damer | 01/17 04:20 | 46 | [155] Shelby Rogers v Caroline Dolehide [141] | 6-4,6-4 | |
| Australian Open - Damer | 01/16 04:10 | 45 | [190] Olga Govortsova v Caroline Dolehide [141] | 3-6,4-6 | |
| Australian Open - Damer | 01/14 00:00 | 44 | [164] Mariam Bolkvadze v Caroline Dolehide [141] | 3-6,2-6 | |
| WTA Auckland | 01/05 01:30 | 46 | [100] Camila Giorgi v Caroline Dolehide [146] | 7-5,6-3 | |
| WTA Auckland | 01/04 02:00 | 45 | [241] Coco Vandeweghe v Caroline Dolehide [146] | 1-6,6-7 | |
| WTA Houston | 11/15 16:00 | 26 | [148] Caroline Dolehide v Taylor Townsend [84] | 7-5,2-6,3-6 | |
| WTA Houston | 11/12 20:50 | 25 | [148] Caroline Dolehide v Giuliana Olmos [404] | 7-5,6-4 | |
| ITF W60 - Las Vegas | 11/08 19:30 | 27 | [154] Caroline Dolehide v Katarina Zavatska [110] | 2-6,6-4,4-6 | |
| ITF W60 - Las Vegas | 11/07 21:45 | 26 | [154] Caroline Dolehide v Natasha Subhash [424] | 6-3,6-3 | |
| ITF W60 - Las Vegas | 11/06 18:55 | 25 | [154] Caroline Dolehide v Vladica Babic [164] | 6-0,6-1 | |
| ITF W80 - Tyler | 11/01 21:30 | 27 | [423] Alexa Glatch v Caroline Dolehide [166] | 7-6,6-1 | |
| ITF W80 - Tyler | 11/01 18:05 | 26 | [192] Katherine Sebov v Caroline Dolehide [166] | 3-6,2-6 | |
| ITF W80 - Tyler | 10/31 18:40 | 25 | [313] Grace Min v Caroline Dolehide [166] | 6-7,6-4,4-6 | |
| ITF W80 - Macon | 10/24 14:00 | 26 | [471] Katerina Stewart v Caroline Dolehide [166] | 6-4,3-6,6-3 | |
| ITF W80 - Macon | 10/23 17:25 | 25 | Estela Perez-Somarriba v Caroline Dolehide | 5-7,4-6 | |
| ITF W60 - Charleston | 10/06 15:30 | 29 | [374] Grace Min v Caroline Dolehide [203] | 2-6,7-6,0-6 | |
| ITF W60 - Charleston | 10/05 17:30 | 28 | [245] Maria C O Serrano v Caroline Dolehide [203] | Retired | |
| ITF W60 - Charleston | 10/04 15:55 | 27 | [261] Marina Melnikova v Caroline Dolehide [203] | 2-6,3-6 | |
| ITF W60 - Charleston | 10/03 14:00 | 26 | Marine Partaud v Caroline Dolehide | 2-6,0-6 | |
| ITF W60 - Charleston | 10/02 19:10 | 25 | [352] Bianca Turati v Caroline Dolehide [203] | 2-6,0-6 | |
| US Open - Damer | 08/27 00:25 | 23 | [214] Caroline Dolehide v Qiang Wang [18] | 4-6,4-6 | |
| US Open - Damer | 08/23 18:05 | 46 | [214] Caroline Dolehide v Anna-Lena Friedsam [231] | 6-4,6-3 | |
| US Open - Damer | 08/22 15:00 | 45 | [168] Zoe Hives v Caroline Dolehide [214] | 1-6,6-7 | |
| US Open - Damer | 08/20 15:00 | 44 | [298] Shelby Rogers v Caroline Dolehide [214] | Retired | |
| ITF W60 - Concord | 08/17 20:00 | 29 | [283] Caroline Dolehide v Ann Li [178] | 6-3,7-5 | |
| ITF W60 - Concord | 08/16 15:00 | 28 | [202] Olga Govortsova v Caroline Dolehide [283] | 6-7,4-6 | |
| ITF W60 - Concord | 08/15 15:00 | 27 | [283] Caroline Dolehide v Ana Bogdan [141] | 6-4,6-3 | |
| ITF W60 - Concord | 08/14 16:00 | 26 | [129] Lin Zhu v Caroline Dolehide [283] | 1-6,1-6 | |
| ITF W60 - Concord | 08/13 18:40 | 25 | [170] Nina Stojanovic v Caroline Dolehide [283] | 1-6,6-3,6-7 | |
| ITF W60 - Berkeley | 07/19 19:10 | 27 | [256] Caroline Dolehide v Sachia Vickery [163] | 3-6,5-7 |