| ITF W25 Guayaquil | 2019/08/21 19:30 | Maria Jose Portillo Ramirez v Katerina Stewart | 6-3,6-7,0-6 |
| UTR Pro Tennis Series Florida Women | 2020/07/05 15:00 | Maria Jose Portillo Ramirez v Jennifer Elie | 5-4 |
| UTR Pro Tennis Series Florida Women | 2020/07/05 12:00 | Maria Jose Portillo Ramirez v Layne Sleeth | 6-7,6-4,4-10 |
| UTR Pro Tennis Series Florida Women | 2020/07/04 15:45 | Hurricane Tyra Black v Maria Jose Portillo Ramirez | 2-6,1-6 |
| UTR Pro Tennis Series Florida Women | 2020/07/02 17:30 | Varvara Lepchenko v Maria Jose Portillo Ramirez | 4-6,6-4,1-0 |
| US Pro Tennis Series East Coast Women | 2020/07/02 14:30 | Varvara Lepchenko v Maria Jose Portillo Ramirez | 4-6,6-4,10-8 |
| UTR Pro Tennis Series Florida Women | 2020/07/02 12:00 | Jovana Jovic v Maria Jose Portillo Ramirez | 6-4,6-0 |
| UTR Pro Tennis Series Florida Women | 2020/06/30 15:45 | Jovana Jovic v Maria Jose Portillo Ramirez | 6-2,6-3 |
| UTR Pro Tennis Series Florida Women | 2020/06/30 13:15 | Maria Jose Portillo Ramirez v Rhiann Newborn | 6-3,6-3 |
| UTR Pro Tennis Series Florida Women | 2020/07/03 14:30 | Mayuka Aikawa v Katerina Stewart | 2-6,1-6 |
| UTR Pro Tennis Series Florida Women | 2020/07/03 12:00 | Quinn Gleason v Katerina Stewart | 2-6,3-6 |
| UTR Pro Tennis Series Florida Women | 2020/07/01 14:30 | Sofia Sewing v Katerina Stewart | 1-6,3-6 |
| UTR Pro Tennis Series Florida Women | 2020/07/01 12:00 | Katerina Stewart v Seone Mendez | 6-4,7-6 |
| UTR Pro Tennis Series Florida Women | 2020/06/29 18:10 | Katerina Stewart v Alycia Parks | 1-6,1-6 |
| UTR Pro Tennis Series Florida Women | 2020/06/29 12:00 | Katerina Stewart v Elizabeth Halbauer | 3-6,7-5,10-5 |
| UTR Pro Tennis Series Florida Women | 2020/06/27 16:10 | Anastasia E Nefedova v Katerina Stewart | 6-4,7-6 |
| UTR Pro Tennis Series Florida Women | 2020/06/27 14:20 | Sachia Vickery v Katerina Stewart | 0-6,1-6 |