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
| Matchplay 120 Women | 2020/05/29 13:00 | Jamie Loeb v Laura Siegemund | 6-1,5-7,1-6 |
| US Pro Tennis Series Women | 2020/05/10 16:45 | Jamie Loeb v Jessica Livianu | 3-0 |
| US Pro Tennis Series Women | 2020/05/10 14:00 | Jamie Loeb v Luisa Stefani | 4-6,5-7 |
| US Pro Tennis Series Women | 2020/05/07 20:15 | Jennifer Elie v Jamie Loeb | 1-6,2-6 |
| US Pro Tennis Series Women | 2020/05/07 16:30 | Jamie Loeb v Sofia Sewing | 6-1,1-6,7-10 |
| WTA Indian Wells | 2020/03/02 23:15 | Kurumi Nara v Jamie Loeb | 7-6,6-4 |
| ITF W25 Rancho Santa Fe | 2020/02/27 21:45 | Yanina Wickmayer v Jamie Loeb | 4-6,6-0,6-0 |
| ITF W25 Rancho Santa Fe | 2020/02/26 18:00 | Jamie Loeb v Alexa Glatch | 7-5,6-2 |
Away History
| Matchplay 120 Women | 2020/05/30 18:00 | Laura Siegemund v Caroline Dolehide | 3-6,4-6 |
| WTA Monterrey | 2020/03/02 23:25 | Olga Govortsova v Caroline Dolehide | 3-6,6-2,6-1 |
| WTA Monterrey | 2020/03/01 22:15 | Lara Arruabarrena v Caroline Dolehide | 6-4,7-6 |
| WTA Monterrey | 2020/02/29 22:00 | Ana Sofia Sanchez v Caroline Dolehide | 3-6,6-4,5-7 |
| WTA Acapulco | 2020/02/27 01:20 | Caroline Dolehide v Christina McHale | 7-5,4-6,3-6 |
| 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 |