Stadium: Court 10 Round: 26 Ground: Hardcourt outdoor
| ITF W15 Cancun | 2019/11/05 19:00 | Maribella Zamarripa v Madison Bourguignon | 6-3,2-6,4-6 |
| ITF W25 Evansville | 2019/07/22 18:00 | Katrina Scott v Madison Bourguignon | 6-1,6-2 |
| ITF W15 Cancun | 2019/07/02 13:30 | Madison Bourguignon v Wijesundera, Rushri | 0-6,5-7 |
| ITF W15 Cancun | 2019/06/27 15:20 | Madison Bourguignon v Thaisa Grana Pedretti | 1-6,2-6 |
| ITF W15 Cancun | 2019/06/25 15:30 | Jennifer Rosa Dourado v Madison Bourguignon | 3-6,3-6 |
| Orlando, Singles Qualifying W-ITF-USA-27A | 2019/06/18 13:00 | Madison Bourguignon v Carruthers, Steffi | 3-6,0-6 |
| Orlando, Singles Qualifying W-ITF-USA-27A | 2019/06/17 13:00 | Alessandra Crump v Madison Bourguignon | 0-6,1-6 |
| ITF W15 Cancun | 2019/05/13 14:30 | Madison Bourguignon v Mamalat, Anna | 1-6,1-6 |
| ITF W15 Cancun | 2019/11/05 17:35 | Sysoeva, Anastasia v Adrienn Nagy | 6-3,6-1 |
| ITF W15 Cancun | 2019/10/31 14:00 | Adrienn Nagy v Sysoeva, Anastasia | 6-1,5-7,6-4 |
| Austin, Singles W-ITF-USA-38B | 2019/10/25 16:00 | Chavatipon, Charlotte v Sysoeva, Anastasia | 6-2,6-1 |
| Austin, Singles W-ITF-USA-38B | 2019/10/24 16:00 | Sysoeva, Anastasia v Fernanda Labrana | 7-6,7-6 |
| Austin, Singles W-ITF-USA-38B | 2019/10/23 21:00 | Kylie Mckenzie v Sysoeva, Anastasia | 6-4,3-6,3-6 |
| Austin, Singles W-ITF-USA-38B | 2019/10/22 15:00 | Sysoeva, Anastasia v Reimchen, Anastasia | 7-6,2-6,10-5 |
| Austin, Singles W-ITF-USA-38B | 2019/10/21 15:00 | Sysoeva, Anastasia v Bulatovic, Carolina | 6-2,6-1 |
| ITF W25 Florence | 2019/10/13 14:00 | Sysoeva, Anastasia v Daniell, Andie K. | 1-6,0-6 |