Stadium: Court 6 Round: 44 Ground: Hardcourt outdoor
| ITF - M15 Monastir | 2021/07/19 09:00 | Sysoev, Nikolay v Joshua Sheehy | 2-6,1-6 |
| ITF M15 Cancun | 2022/01/20 17:45 | Sysoev, Nikolay v Alex Hernandez | 2-6,3-6 |
| ITF M15 Cancun | 2022/01/19 14:45 | Sysoev, Nikolay v Winter Meagher | 6-1,6-2 |
| ITF M15 Cancun | 2022/01/18 14:00 | Andres Urrea v Sysoev, Nikolay | 3-6,7-5,5-10 |
| ITF M15 Cancun | 2022/01/17 16:30 | Gal Emersic Potocnik v Sysoev, Nikolay | 4-6,3-6 |
| ITF M15 Cancun | 2022/01/16 17:30 | Pedro Cressoni v Sysoev, Nikolay | 6-7,4-6 |
| UTR Pro Tennis Series Florida | 2022/01/08 20:30 | Sysoev, Nikolay v Alexander Brown | 4-6,6-4,6-7 |
| UTR Pro Tennis Series Florida | 2022/01/07 19:30 | Gold, Harrison v Sysoev, Nikolay | 0-6,3-4 |
| UTR Pro Tennis Series Florida | 2022/01/06 14:00 | Johnson, Janmagnus v Sysoev, Nikolay | 6-4,6-4 |
| ITF M15 Cancun | 2022/01/19 14:45 | Joshua Sheehy v Chahoud, Kevin | 3-6,4-6 |
| ITF M15 Cancun | 2021/12/15 14:30 | Joshua Sheehy v Alexander Bernard | 6-7,2-6 |
| ITF M15 Cancun | 2021/12/14 17:00 | Gregg, Perry v Joshua Sheehy | 6-2,6-4 |
| ITF M15 Cancun | 2021/12/13 18:00 | Marcelo Marino Hidalgo v Joshua Sheehy | 2-6,2-6 |
| ITF M15 Cancun | 2021/12/06 14:00 | Joshua Sheehy v Kiranpal Pannu | 4-6,4-6 |
| ITF M15 Cancun | 2021/12/04 14:00 | Nam Hoang Ly v Joshua Sheehy | 6-2,6-2 |
| ITF M15 Cancun | 2021/12/02 17:00 | Joshua Sheehy v Luis Britto | 6-2,6-0 |
| ITF M15 Cancun | 2021/11/30 16:00 | Ren Nakamura v Joshua Sheehy | 6-7,0-6 |