Stadium: Court 3 Round: 26 Ground: Hardcourt outdoor
| ITF W80 Macon | 2019/10/23 16:00 | Hanna Chang v Stewart, Katerina | 6-0,6-7,2-6 |
| ITF W25 Florence | 2019/10/17 14:00 | Stewart, Katerina v Emma Navarro | 6-2,4-6,5-7 |
| ITF W25 Florence | 2019/10/16 17:00 | Larsson, Johanna v Stewart, Katerina | 3-6,4-6 |
| ITF W25 Hilton Head Island | 2019/10/10 14:00 | Stewart, Katerina v Panna Udvardy | 3-6,4-6 |
| ITF W25 Hilton Head Island | 2019/10/08 15:35 | Stewart, Katerina v Sanesi, Gaia | 6-3,5-7,6-3 |
| ITF W60 Charleston | 2019/09/30 20:10 | Stewart, Katerina v Maria Mateas | 1-6,6-3,3-10 |
| ITF W25 Guayaquil | 2019/08/25 16:00 | Stewart, Katerina v Maria Camila Osorio Serrano | 5-7,3-6 |
| ITF W25 Guayaquil | 2019/08/24 16:00 | Stewart, Katerina v Chieh-Yu Hsu | 6-7,6-3,6-2 |
| ITF W80 Macon | 2019/10/23 17:25 | Perez-Somarriba, Estela v Caroline Dolehide | 5-7,4-6 |
| ITF W60 Charleston | 2019/10/06 15:30 | Grace Min v Caroline Dolehide | 2-6,7-6,0-6 |
| ITF W60 Charleston | 2019/10/04 15:55 | Marina Melnikova v Caroline Dolehide | 2-6,3-6 |
| ITF W60 Charleston | 2019/10/03 14:00 | Marine Partaud v Caroline Dolehide | 2-6,0-6 |
| ITF W60 Charleston | 2019/10/02 19:10 | Turati, Bianca v Caroline Dolehide | 2-6,0-6 |
| US Open Women | 2019/08/27 00:25 | Caroline Dolehide v Qiang Wang | 4-6,4-6 |
| US Open Women | 2019/08/23 18:05 | Caroline Dolehide v Anna-Lena Friedsam | 6-4,6-3 |
| US Open Women | 2019/08/22 15:00 | Zoe Hives v Caroline Dolehide | 1-6,6-7 |