| WTA Quebec City | 09/13 21:00 | 26 | Caroline Dolehide v Oceane Dodin | Walkover | |
| WTA Quebec City | 09/11 17:00 | 25 | [307] Charlotte Robillard-Millette v Caroline Dolehide [161] | 3-6,2-6 | |
| WTA Quebec City Qual | 09/10 14:00 | 46 | [161] Caroline Dolehide v Victoria Rodriguez [269] | 6-4,6-2 | |
| WTA Quebec City Qual | 09/09 14:00 | 45 | [161] Caroline Dolehide v Alexa Guarachi [414] | 6-7,6-0,6-1 | |
| US Open Women Qual | 08/23 20:55 | 44 | [159] Caroline Dolehide v Claire Liu [293] | 1-6,2-6 | |
| WTA Cincinnati Qual | 08/12 17:25 | 44 | [162] Caroline Dolehide v Magda Linette [83] | 7-6,6-7,6-7 | |
| WTA - Stanford | 08/02 20:00 | 26 | [21] Madison Keys v Caroline Dolehide [212] | 3-6,6-2,6-3 | |
| WTA - Stanford | 08/01 17:00 | 25 | [212] Caroline Dolehide v Naomi Osaka [48] | 6-4,6-2 | |
| WTA Stanford Qual | 07/30 17:00 | - | [161] Lizette Cabrera v Caroline Dolehide [212] | 6-4,3-6,4-6 | |
| WTA Stanford Qual | 07/29 17:00 | 26 | [302] Gabriela Dabrowski v Caroline Dolehide [212] | 1-6,2-6 | |
| ITF Women Sacramento | 07/27 19:00 | 26 | [212] Caroline Dolehide v Kristie Ahn [116] | 1-6,6-7 | |
| ITF Women Sacramento | 07/26 17:00 | 25 | [253] Tessah Andrianjafitrimo v Caroline Dolehide [212] | 3-6,0-6 | |
| ITF Women Stockton | 07/20 16:00 | 26 | [251] Caroline Dolehide v Jamie Loeb [154] | 3-6,2-6 | |
| ITF Women Stockton | 07/19 17:30 | 25 | [251] Caroline Dolehide v Chanel Simmonds [345] | 6-3,6-4 | |
| ITF Women Winnipeg | 07/16 16:00 | 29 | [250] Mayo Hibi v Caroline Dolehide [246] | 3-6,4-6 | |
| ITF Women Winnipeg | 07/15 16:00 | 28 | [246] Caroline Dolehide v Shilin Xu [285] | 6-2,6-3 | |
| ITF Women Winnipeg | 07/14 15:00 | 27 | [330] Miharu Imanishi v Caroline Dolehide [246] | 7-6,4-6,6-7 | |
| ITF Women Winnipeg | 07/12 19:30 | 26 | Kimberly Birrell v Caroline Dolehide | 6-4,2-6,4-6 | |
| ITF Women Winnipeg | 07/10 16:40 | 25 | Sara Daavettila v Caroline Dolehide | 3-6,2-6 | |
| ITF Women Ilkley | 06/21 12:10 | 25 | [233] Caroline Dolehide v Alison Van Uytvanck [103] | 3-6,3-6 | |
| ITF Women Ilkley Qual | 06/20 09:30 | 54 | [192] Bianca Andreescu v Caroline Dolehide [233] | 3-6,6-7 | |
| ITF Women Ilkley Qual | 06/19 10:00 | 54 | [173] Destanee Aiava v Caroline Dolehide [233] | 6-7,3-6 | |
| ITF Women Ilkley Qual | 06/18 11:50 | 54 | [242] Caroline Dolehide v Arina Rodionova [165] | 2-6,6-3,6-4 | |
| WTA Nottingham Qual | 06/11 12:55 | 46 | [164] Elizaveta Kulichkova v Caroline Dolehide [239] | 6-7,6-3,6-4 | |
| WTA Nottingham Qual | 06/10 14:20 | 45 | Alexandra Stevenson v Caroline Dolehide | 3-6,4-6 | |
| ITF Women Surbiton | 06/07 14:00 | 25 | [275] Karolina Muchova v Caroline Dolehide [239] | 4-6,6-4,7-6 | |
| ITF Women Charleston | 05/03 15:15 | 25 | [98] Madison Brengle v Caroline Dolehide [252] | 6-4,6-2 | |
| ITF Women Charlottesville | 04/30 16:00 | 29 | [98] Madison Brengle v Caroline Dolehide [252] | 6-4,6-3 | |
| ITF Women Charlottesville | 04/29 15:45 | 28 | [359] Ajla Tomljanovic v Caroline Dolehide [252] | 1-6,6-7 | |
| ITF Women Charlottesville | 04/28 16:40 | 27 | [324] Catalina Pella v Caroline Dolehide [252] | 4-6,6-4,4-6 |