| Australian Open - ženy | 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 | |
| ITF W80 Tyler | 10/29 16:45 | 25 | [156] Sachia Vickery v Caroline Dolehide [148] | 1-6,3-6 | |
| ITF W80 Macon | 10/22 14:00 | 25 | Caroline Dolehide v Astra Sharma | Cancelled | |
| ITF W80 Macon | 10/21 13:50 | 25 | [148] Caroline Dolehide v Katie Volynets [325] | 6-7,3-6 | |
| French Open - ženy | 09/22 13:35 | 14 | [181] Mayo Hibi v Caroline Dolehide [140] | 3-6,7-5,7-5 | |
| US Open - ženy | 08/31 17:10 | 23 | [135] Caroline Dolehide v Anna-Lena Friedsam [109] | 2-6,2-6 | |
| WTA New York | 08/21 15:00 | 19 | [67] Laura Siegemund v Caroline Dolehide [136] | 6-3,6-3 | |
| WTA New York | 08/20 16:35 | 44 | [136] Caroline Dolehide v Jasmine Paolini [96] | 6-3,2-6,6-4 | |
| WTA Lexington | 08/11 17:40 | 25 | [134] Caroline Dolehide v Cori Gauff [53] | 5-7,5-7 |