Stadium: Court 10 Round: 44 Ground: Hardcourt outdoor
| ITF M25 Naples | 2019/10/27 14:00 | Mehdi Laalej v Nikolay Sysoev | 6-2,6-1 |
| ITF M15 Cancun | 2019/08/26 15:30 | Nikolay Sysoev v Logan Smith | 1-6,2-6 |
| ITF M15 Cancun | 2019/08/19 14:30 | Miles Jones v Nikolay Sysoev | 6-0,6-1 |
| ITF M15 Cancun | 2019/08/14 15:35 | Nicholas Shamma v Nikolay Sysoev | 6-1,6-0 |
| ITF M15 Cancun | 2019/08/12 17:00 | Kalman Boyd v Nikolay Sysoev | 6-1,6-1 |
| ITF M15 Cancun | 2019/07/08 17:30 | Nicholas Reyes v Nikolay Sysoev | 6-0,6-3 |
| ITF M15 Cancun | 2019/07/01 13:30 | Aron Pierce v Nikolay Sysoev | 6-1,6-1 |
| ITF M15 Cancun | 2019/06/24 13:30 | Zakai Stone v Nikolay Sysoev | 6-1,0-6,10-6 |
| ITF M15 Cancun | 2019/12/08 14:00 | Yuki Ikeda v Joao Victor Ortega | 6-0,6-1 |
| ITF M15 Cancun | 2019/12/01 16:00 | Joao Victor Ortega v Floris Podzimek | 0-6,0-6 |
| ITF M15 Cancun | 2019/11/17 15:30 | Camilo A Alvarez Vergara v Joao Victor Ortega | 6-4,5-7,10-7 |
| ITF M15 Cancun | 2019/11/03 16:00 | Lance A L Castelan v Joao Victor Ortega | 7-5,6-0 |
| ITF M15 Cancun | 2019/09/22 18:30 | Joao Victor Ortega v Erick Sanchez | 1-6,3-6 |
| ITF M15 Cancun | 2019/08/26 14:30 | Joao Victor Ortega v Nicholas Shamma | 0-6,0-6 |
| ITF M15 Cancun | 2019/06/25 15:00 | Joao Victor Ortega v Juan A H Serrano | 0-6,0-6 |
| ITF M15 Cancun | 2019/05/13 13:30 | Joao Victor Ortega v Nicholas Bybel | 0-6,0-6 |