Head to Head
| ITF W100 Surbiton | 2019/06/03 10:00 | Jamie Loeb v Caroline Dolehide | 4-6,3-6 |
| ITF Women Stockton | 2017/07/20 16:00 | Caroline Dolehide v Jamie Loeb | 3-6,2-6 |
Home History
| 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 |
| Australian Open Women | 2020/01/17 04:20 | Shelby Rogers v Caroline Dolehide | 6-4,6-4 |
| Australian Open Women | 2020/01/16 04:10 | Olga Govortsova v Caroline Dolehide | 3-6,4-6 |
| Australian Open Women | 2020/01/14 00:00 | Mariam Bolkvadze v Caroline Dolehide | 3-6,2-6 |
| WTA Auckland | 2020/01/05 01:30 | Camila Giorgi v Caroline Dolehide | 7-5,6-3 |
| WTA Auckland | 2020/01/04 02:00 | Coco Vandeweghe v Caroline Dolehide | 1-6,6-7 |
Away History
| ITF W100 Nicholasville | 2020/02/12 21:55 | Jamie Loeb v Anhelina Kalinina | 2-6,6-7 |
| ITF W100 Nicholasville | 2020/02/11 17:00 | Francoise Abanda v Jamie Loeb | 2-6,6-4,8-10 |
| ITF W100 Nicholasville | 2020/02/10 18:45 | Sophie Chang v Jamie Loeb | 0-6,0-6 |
| ITF W100 Midland | 2020/02/08 19:55 | Jamie Loeb v Anhelina Kalinina | 0-6,1-6 |
| ITF W100 Midland | 2020/02/07 19:00 | Jamie Loeb v Catherine Harrison | 6-4,6-3 |
| ITF W100 Midland | 2020/02/06 16:55 | Robin Anderson v Jamie Loeb | 3-6,6-4,2-6 |
| ITF W100 Midland | 2020/02/04 19:55 | Jamie Loeb v Mona Barthel | 7-5,4-6,6-4 |
| WTA Newport Beach | 2020/01/27 23:50 | Jamie Loeb v Claire Liu | 4-6,2-6 |