Stadium: Court 1 Round: 1
| US Pro Tennis Series Women | 2020/05/30 11:00 | Stewart, Katerina v Mayuka Aikawa | 6-0,6-1 |
| US Pro Tennis Series Women | 2020/05/28 15:25 | Stewart, Katerina v van Nguyen, Chanelle | 6-2,3-6,10-7 |
| US Pro Tennis Series Women | 2020/05/28 12:00 | Stewart, Katerina v Renata Zarazua | 2-6,3-6 |
| US Pro Tennis Series Women | 2020/05/27 18:10 | Xu, Shilin v Stewart, Katerina | 1-6,6-4,11-13 |
| US Pro Tennis Series Women | 2020/05/27 14:20 | Livianu, Jessica v Stewart, Katerina | 4-6,1-6 |
| US Pro Tennis Series Women | 2020/05/17 23:00 | Stewart, Katerina v Talaba, Gabriela | 5-7,5-7 |
| US Pro Tennis Series Women | 2020/05/17 18:15 | Stewart, Katerina v Nefedova, Anastasia Evgenyevna | 3-6,6-1,12-10 |
| US Pro Tennis Series Women | 2020/05/16 22:00 | Stewart, Katerina v Renata Zarazua | 3-6,4-6 |
| US Pro Tennis Series Women | 2020/05/30 11:00 | Renata Zarazua v Gleason, Quinn | 6-3,6-2 |
| US Pro Tennis Series Women | 2020/05/28 17:30 | Panna Udvardy v Gleason, Quinn | 3-6,1-6 |
| US Pro Tennis Series Women | 2020/05/28 13:55 | Gleason, Quinn v Jovic, J. | 2-6,4-6 |
| US Pro Tennis Series Women | 2020/05/26 13:35 | Alycia Parks v Gleason, Quinn | 1-6,0-6 |
| US Pro Tennis Series Women | 2020/05/25 16:30 | Black, Hurricane Tyra v Gleason, Quinn | 6-3,6-4 |
| Nicholasville, Singles Qualifying W-ITF-USA-05A | 2020/02/11 16:55 | Grace Min v Gleason, Quinn | 6-4,6-2 |
| Nicholasville, Singles Qualifying W-ITF-USA-05A | 2020/02/10 19:20 | Gleason, Quinn v Ana Sofia Sanchez | 6-4,5-7,10-7 |
| Midland, Simples W-ITF-USA-03A | 2020/02/05 16:00 | Xu, Shilin v Gleason, Quinn | 6-0,6-3 |