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