Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| ITF W15 Cancun | 2019/11/07 14:00 | Bourguignon, Madison v Sysoeva, Anastasia | 4-6,6-3,4-6 |
| ITF W25 Naples | 2019/11/18 14:00 | Emma Navarro v Sysoeva, Anastasia | 6-0,6-2 |
| ITF W25 Naples | 2019/11/17 14:00 | Sysoeva, Anastasia v Tchakarova, Eleonore | 6-2,6-7,10-5 |
| ITF W15 Cancun | 2019/11/09 14:00 | Maria Jose Portillo Ramirez v Sysoeva, Anastasia | 6-2,6-2 |
| ITF W15 Cancun | 2019/11/08 16:15 | Hosonuma, Chisa v Sysoeva, Anastasia | 6-1,5-7,2-6 |
| ITF W15 Cancun | 2019/11/07 14:00 | Bourguignon, Madison v Sysoeva, Anastasia | 4-6,6-3,4-6 |
| 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 |
| ITF W15 Cancun | 2019/11/17 15:00 | Pitts, Maya v Bourguignon, Madison | 6-4,6-0 |
| ITF W15 Cancun | 2019/11/07 14:00 | Bourguignon, Madison v Sysoeva, Anastasia | 4-6,6-3,4-6 |
| ITF W15 Cancun | 2019/11/05 19:00 | Maribella Zamarripa v Bourguignon, Madison | 6-3,2-6,4-6 |
| ITF W25 Evansville | 2019/07/22 18:00 | Katrina Scott v Bourguignon, Madison | 6-1,6-2 |
| ITF W15 Cancun | 2019/07/02 13:30 | Bourguignon, Madison v Wijesundera, Rushri | 0-6,5-7 |
| ITF W15 Cancun | 2019/06/27 15:20 | Bourguignon, Madison v Thaisa Grana Pedretti | 1-6,2-6 |
| ITF W15 Cancun | 2019/06/25 15:30 | Jennifer Rosa Dourado v Bourguignon, Madison | 3-6,3-6 |
| Orlando, Singles Qualifying W-ITF-USA-27A | 2019/06/18 13:00 | Bourguignon, Madison v Carruthers, Steffi | 3-6,0-6 |