Stadium: Court 7 Round: 44 Ground: Hardcourt outdoor
| ITF - M15 Santo Domingo | 2019/12/12 14:40 | A.J Catanzariti v Jose Olivares | 7-6,6-4 |
| ITF - M15 Santo Domingo | 2019/12/11 16:00 | Alex Blumenberg v Jose Olivares | 3-6,1-6 |
| ITF - M15 Santo Domingo | 2019/12/06 15:50 | Jan Choinski v Jose Olivares | 6-1,6-4 |
| ITF - M15 Santo Domingo | 2019/12/05 14:00 | Fletcher Scott v Jose Olivares | 1-6,3-6 |
| ITF - M15 Santo Domingo | 2019/12/04 16:05 | Jose Olivares v Mauricio Echazu | 6-4,3-6,6-3 |
| ITF - M15 Santo Domingo | 2019/11/29 14:00 | Nick Hardt v Jose Olivares | 5-7,6-2,7-6 |
| ITF - M15 Santo Domingo | 2019/11/28 15:30 | Jose Olivares v Gage Brymer | 6-7,6-4,6-4 |
| ITF - M15 Santo Domingo | 2019/11/27 16:45 | Matthew Mendez v Jose Olivares | 3-6,1-6 |
| ITF - M25 Naples | 2020/02/09 15:00 | Nikolay Sysoev v Daniel Vrba | 1-6,3-6 |
| ITF - M15 Cancun | 2020/01/26 19:00 | Osgar O'Hoisin v Nikolay Sysoev | 6-0,6-1 |
| ITF - M15 Cancun | 2020/01/19 15:30 | Alexander Lebedev v Nikolay Sysoev | 6-2,6-2 |
| ITF - M15 Cancun | 2020/01/12 17:30 | Yeudy Villar v Nikolay Sysoev | 6-3,6-2 |
| ITF - M15 Cancun | 2020/01/12 14:00 | Nikolay Sysoev v Joao Victor Ortega | 6-1,6-0 |
| 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 |