stadio: Court 8 Round: 62 Ground: Hardcourt outdoor
| 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 |
| ITF M15 Antalya | 2021/06/20 07:00 | Fletcher Scott v Nikolay Sysoev | 6-1,7-5 |
| ITF M15 Antalya | 2021/06/14 07:30 | Nikolay Sysoev v Daniel Antonio Nunez | 2-6,3-6 |
| ITF M15 Antalya | 2021/06/13 07:30 | Suleyman Deniz Gursoy v Nikolay Sysoev | 2-6,4-6 |
| ITF M15 Monastir | 2021/07/18 09:00 | Aleksandr Lobanov v Joshua Sheehy | 4-6,4-6 |
| ITF M15 Monastir | 2021/07/12 09:00 | Connor Di Marco v Joshua Sheehy | 7-6,6-4 |
| ITF M15 Monastir | 2021/07/11 11:00 | Nikolas Moceanu v Joshua Sheehy | 6-7,5-7 |
| ITF M25 Weston | 2021/06/28 19:00 | Alan Kohen v Joshua Sheehy | 6-2,6-3 |
| ITF M15 Champaign | 2021/06/21 15:00 | Connor Farren v Joshua Sheehy | 6-3,6-4 |
| ITF M25 Tulsa | 2021/06/14 18:00 | Nathan Ponwith v Joshua Sheehy | 6-3,6-4 |
| ITF M25 Wichita | 2021/06/07 15:00 | Matt Kuhar v Joshua Sheehy | 6-4,7-6 |
| UTR Pro Tennis Series California | 2021/05/23 15:00 | Kyle Kang v Joshua Sheehy | 7-5,6-3 |