Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| ITF W15 Cancun | 2019/11/07 14:00 | Madison Bourguignon v Anastasia Sysoeva | 4-6,6-3,4-6 |
| ITF W25 Naples | 2019/11/18 14:00 | Emma Navarro v Anastasia Sysoeva | 6-0,6-2 |
| ITF W25 Naples | 2019/11/17 14:00 | Anastasia Sysoeva v Eleonore Tchakarova | 6-2,6-7,10-5 |
| ITF W15 Cancun | 2019/11/09 14:00 | Maria Jose Portillo Ramirez v Anastasia Sysoeva | 6-2,6-2 |
| ITF W15 Cancun | 2019/11/08 16:15 | Chisa Hosonuma v Anastasia Sysoeva | 6-1,5-7,2-6 |
| ITF W15 Cancun | 2019/11/07 14:00 | Madison Bourguignon v Anastasia Sysoeva | 4-6,6-3,4-6 |
| ITF W15 Cancun | 2019/11/05 17:35 | Anastasia Sysoeva v Adrienn Nagy | 6-3,6-1 |
| ITF W15 Cancun | 2019/10/31 14:00 | Adrienn Nagy v Anastasia Sysoeva | 6-1,5-7,6-4 |
| ITF W15 Austin | 2019/10/25 16:00 | Charlotte Chavatipon v Anastasia Sysoeva | 6-2,6-1 |
| ITF W15 Cancun | 2019/11/17 15:00 | Maya Pitts v Madison Bourguignon | 6-4,6-0 |
| ITF W15 Cancun | 2019/11/07 14:00 | Madison Bourguignon v Anastasia Sysoeva | 4-6,6-3,4-6 |
| 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 Rushri Wijesundera | 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 |
| ITF W15 Orlando | 2019/06/18 13:00 | Madison Bourguignon v Steffi Carruthers | 3-6,0-6 |