| ITF M15 Monastir | 2021/08/01 09:00 | Drew Baird v Nikolay Sysoev | 6-1,6-2 |
| ITF M15 Monastir | 2021/07/25 08:00 | Nikolay Sysoev v Austin Ansari | 2-6,0-6 |
| ITF M15 Monastir | 2021/07/19 09:00 | Nikolay Sysoev v Joshua Sheehy | 2-6,1-6 |
| ITF M15 Monastir | 2021/07/18 09:00 | Fermin Calvo Barcelo v Nikolay Sysoev | 3-6,6-4,6-10 |
| ITF M15 Monastir | 2021/07/11 09:00 | Evgeny Philippov v Nikolay Sysoev | 6-2,6-1 |
| ITF M15 Monastir | 2021/07/05 09:00 | Lorenzo Rottoli v Nikolay Sysoev | 6-1,6-4 |
| ITF M15 Antalya | 2021/06/28 10:50 | Vladimir Korolev v Nikolay Sysoev | 6-1,6-0 |
| ITF M15 Antalya | 2021/06/27 06:30 | Nikolay Sysoev v Jason Janis | 6-3,6-4 |
| UTR Pro Tennis Series Florida | 2021/08/28 13:30 | Omar Maldonado v Mateo Barreiros Reyes | 3-6,4-5 |
| UTR Pro Tennis Series Florida | 2021/08/25 13:00 | Omar Maldonado v Henry Lieberman | 6-3,4-6,4-6 |
| UTR Pro Tennis Series Florida | 2021/08/24 13:30 | Omar Maldonado v Juan David Velasquez | 6-1,3-6,3-5 |
| UTR Pro Tennis Series Florida | 2021/08/23 15:00 | Omar Maldonado v Theo Winegar | 6-4,5-3 |
| UTR Pro Tennis Series Florida | 2021/01/15 17:00 | Matt Kuhar v Omar Maldonado | 6-0,6-3 |
| UTR Pro Tennis Series Florida | 2021/01/13 14:00 | Nico Mostardi v Omar Maldonado | 4-6,4-6 |
| UTR Pro Tennis Series Florida | 2021/01/12 20:00 | Noah Rubin v Omar Maldonado | 6-1,5-2 |
| UTR Pro Tennis Series Florida | 2021/01/11 14:00 | John Bernard v Omar Maldonado | 6-0,5-4 |