Stadium: Court 11 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Vero Beach | 2021/10/19 16:00 | Diogo Marques v Nikolay Sysoev | 6-2,6-4 |
| ITF M25 Vero Beach | 2021/10/18 16:00 | Nikolay Sysoev v Jordan Parker | 6-2,6-7,10-7 |
| 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 Carrara | 2021/11/06 03:30 | Robert Stirling v Winter Meagher | 6-3,4-1 |
| UTR Pro Tennis Series Carrara | 2021/11/05 00:30 | Winter Meagher v Thomas Braithwaite | 4-6,6-3,6-4 |
| UTR Pro Tennis Series Carrara | 2021/11/03 00:30 | Winter Meagher v Patrick C Beadman | 3-6,7-6,5-0 |
| UTR Pro Tennis Series Carrara | 2021/11/02 00:30 | Winter Meagher v Sam Ryan Ziegann | 5-7,7-6,5-3 |
| UTR Pro Tennis Series Carrara | 2021/11/01 02:00 | Akira Santillan v Winter Meagher | 6-2,6-4 |
| UTR Pro Tennis Series Carrara | 2021/10/16 02:00 | Winter Meagher v Dusan Rsovac | 3-6,2-6 |
| UTR Pro Tennis Series Carrara | 2021/10/15 02:00 | Winter Meagher v Thomas Nicholas Gadecki | 6-7,4-5 |
| UTR Pro Tennis Series Carrara | 2021/10/12 23:00 | Winter Meagher v Ken Cavrak | 3-6,4-6 |