Stadium: Center Court Round: 54 Ground: Clay
| ITF W25 Osprey | 2019/04/25 15:55 | Alexa Glatch v Olivia Rogowska | 6-1,6-1 |
| ITF W25 Osprey | 2019/04/24 16:10 | Sophie Chang v Olivia Rogowska | 6-2,4-6,6-7 |
| ITF W80 Dothan | 2019/04/16 16:25 | Olivia Rogowska v Gabriela Talaba | 6-7,3-6 |
| ITF W80 Dothan | 2019/04/15 15:00 | Olivia Rogowska v Joelle Kissell | 6-3,6-3 |
| ITF W25 Canberra | 2019/03/31 00:00 | Priscilla Hon v Olivia Rogowska | 6-7,3-6 |
| ITF W25 Canberra | 2019/03/30 00:00 | Olivia Rogowska v Abbie Myers | 6-3,4-6,6-4 |
| ITF W25 Canberra | 2019/03/29 03:00 | Leylah Annie Fernandez v Olivia Rogowska | 6-7,6-1,3-6 |
| ITF W25 Canberra | 2019/03/28 01:45 | Olivia Rogowska v Haruka Kaji | 6-3,6-2 |
| ITF W100 Charleston | 2019/04/29 17:25 | Emerald Able v Cori Gauff | 1-6,0-6 |
| ITF W80 Charlottesville | 2019/04/23 15:50 | Zoe Hives v Cori Gauff | 6-4,7-6 |
| WTA Miami | 2019/03/22 18:20 | Daria Kasatkina v Cori Gauff | 6-3,6-2 |
| WTA Miami | 2019/03/21 16:15 | Cori Gauff v Caty McNally | 3-6,6-3,6-4 |
| WTA Indian Wells | 2019/02/25 22:10 | Timea Bacsinszky v Cori Gauff | 6-3,1-6,6-4 |
| ITF W25 Surprise | 2019/02/17 18:00 | Cori Gauff v Sesil Karatantcheva | 7-5,3-6,1-6 |
| ITF W25 Surprise | 2019/02/16 19:10 | Olga Govortsova v Cori Gauff | 3-6,6-0,3-6 |
| ITF W25 Surprise | 2019/02/15 23:00 | Cori Gauff v Ann Li | 6-4,7-5 |