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