Stadium: Court 2 Round: 54 Ground: Clay
| ITF M15 Naples | 2021/10/12 13:30 | Tristan McCormick v Sysoev, Nikolay | 4-6,6-4,10-5 |
| ITF M15 Naples | 2021/10/11 14:30 | Lawrence, Xavier v Sysoev, Nikolay | 7-6,3-6,3-10 |
| ITF M15 Naples | 2021/10/07 13:30 | Sysoev, Nikolay v Galarza, Juan Ignacio | 1-6,1-6 |
| ITF M15 Naples | 2021/10/06 13:30 | Sysoev, Nikolay v Scott, Fletcher | 6-4,6-4 |
| ITF M15 Naples | 2021/10/05 13:30 | Jake Krug v Sysoev, Nikolay | 6-4,2-6,6-10 |
| ITF M15 Naples | 2021/10/04 14:00 | Parth Aggarwal v Sysoev, Nikolay | 2-6,5-7 |
| UTR Pro Tennis Series Florida | 2021/09/19 15:30 | Sysoev, Nikolay v Phung, Timothy | 7-5,1-6,5-3 |
| UTR Pro Tennis Series Florida | 2021/09/18 18:30 | Noureldin Adam v Sysoev, Nikolay | 3-6,5-6 |
| ITF M25 Pretoria | 2021/09/28 06:55 | Parker, Jordan v Nel, Anro | 3-6,3-6 |
| ITF M25 Pretoria | 2021/09/27 10:00 | Parker, Jordan v Seely, Seth | 7-5,6-2 |
| ITF M25 Johannesburg | 2021/09/20 07:00 | Parker, Jordan v Kruger, Connor | 2-6,3-6 |
| ITF M25 Johannesburg Qual | 2021/09/19 08:10 | Parker, Jordan v Kotze, Da-Niel | 6-3,7-5 |
| ITF M25 Johannesburg | 2021/09/13 07:30 | Parker, Jordan v Friedler, Asaf | 4-6,7-5,8-10 |
| ITF M25 Johannesburg | 2021/09/12 07:25 | Parker, Jordan v Kruger, Connor | 6-3,6-4 |
| ITF M15 Edwardsville | 2021/07/20 14:30 | Stalder, Reese v Parker, Jordan | 6-4,6-0 |
| ITF M25 Weston | 2021/06/28 19:00 | Parker, Jordan v Kiranpal Pannu | 3-6,6-3,9-11 |