Estadio: Cancha 3 Round: 26 Ground: Hardcourt outdoor
| WTA Acapulco | 2020/02/26 03:05 | Usue Maitane Arconada v Caroline Dolehide | 2-6,2-6 |
| WTA Acapulco | 2020/02/23 22:00 | Giulia Gatto Monticone v Caroline Dolehide | 1-6,6-7 |
| WTA Acapulco | 2020/02/22 22:00 | Martina Trevisan v Caroline Dolehide | 6-4,3-6,2-6 |
| ITF W100 Nicholasville | 2020/02/12 23:55 | Claire Liu v Caroline Dolehide | 6-1,6-4 |
| ITF W100 Midland | 2020/02/06 18:30 | Caroline Dolehide v Irina Falconi | 6-1,1-6,1-6 |
| ITF W100 Midland | 2020/02/05 18:40 | Caroline Dolehide v Grace Min | 6-1,6-4 |
| Open de Australia - Femenino | 2020/01/17 04:20 | Shelby Rogers v Caroline Dolehide | 6-4,6-4 |
| Open de Australia - Femenino | 2020/01/16 04:10 | Olga Govortsova v Caroline Dolehide | 3-6,4-6 |
| WTA Acapulco | 2020/02/26 02:45 | Christina McHale v Lauren Davis | 6-2,1-6,6-4 |
| WTA Newport Beach | 2020/01/31 18:00 | Stefanie Voegele v Christina McHale | 6-1,1-6,6-4 |
| WTA Newport Beach | 2020/01/30 18:00 | Sophia Whittle v Christina McHale | 4-6,3-6 |
| WTA Newport Beach | 2020/01/28 20:25 | Grace Min v Christina McHale | 5-7,4-6 |
| Open de Australia - Femenino | 2020/01/20 00:00 | Christina McHale v Petra Martic | 3-6,0-6 |
| WTA Hobart | 2020/01/14 07:40 | Elise Mertens v Christina McHale | 6-1,6-1 |
| WTA Hobart | 2020/01/12 03:35 | Christina McHale v Arantxa Rus | 6-4,4-6,6-3 |
| WTA Hobart | 2020/01/11 04:25 | Christina McHale v Renata Voracova | 6-0,6-2 |