Stadium: Court 1 Round: 29 Ground: Hardcourt outdoor
| ITF W80 Macon | 2019/10/26 16:30 | Stewart, Katerina v Lao, Danielle | 6-3,6-0 |
| ITF W80 Macon | 2019/10/25 15:20 | Falconi, Irina v Stewart, Katerina | 4-6,6-7 |
| ITF W80 Macon | 2019/10/24 14:00 | Stewart, Katerina v Caroline Dolehide | 6-4,3-6,6-3 |
| 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 W80 Macon | 2019/10/26 16:30 | Shelby Rogers v Grace Min | 6-4,6-2 |
| ITF W80 Macon | 2019/10/25 13:55 | Shelby Rogers v Vandeweghe, Coco | 6-0,6-0 |
| ITF W80 Macon | 2019/10/24 16:20 | Usue Maitane Arconada v Shelby Rogers | 0-6,1-6 |
| ITF W80 Macon | 2019/10/23 18:05 | Shelby Rogers v Gabriella Price | 6-4,6-1 |
| WTA Luxembourg | 2019/10/14 16:15 | Shelby Rogers v Tatjana Maria | 3-6,6-1,4-6 |
| WTA - Linz | 2019/10/07 08:00 | Shelby Rogers v Anna-Lena Friedsam | 3-6,6-4,3-6 |
| WTA - Linz | 2019/10/06 09:35 | Flipkens, Kirsten v Shelby Rogers | 3-6,2-6 |
| ITF W60 Templeton | 2019/09/29 20:00 | Shelby Rogers v Vandeweghe, Coco | 4-6,6-2,6-3 |