Stadium: Court 8 Round: 62 Ground: Clay
| ITF - M15 Skopje | 2021/06/06 07:30 | Paul Valsecchi v Leonid Sheyngezikht | 6-7,4-6 |
| ITF - M15 Skopje | 2021/05/30 07:00 | Louis Allen v Leonid Sheyngezikht | 6-4,7-5 |
| ITF - M15 St Petersburg - Calificari | 2021/04/11 11:00 | Leonid Sheyngezikht v Alexander Zgirovsky | 6-4,4-6,4-10 |
| ITF - M15 St Petersburg | 2021/04/05 07:00 | Leonid Sheyngezikht v Alexandr Binda | 2-6,4-6 |
| ITF - M15 St Petersburg | 2021/04/04 11:55 | Alafia Ayeni v Leonid Sheyngezikht | 4-6,2-6 |
| ITF - M15 Kazan | 2021/03/08 07:00 | Daniel Ibragimov v Leonid Sheyngezikht | 4-6,6-4,10-8 |
| ITF - M15 St Petersburg - Calificari | 2021/02/07 10:00 | Alexander Cozbinov v Leonid Sheyngezikht | 6-4,6-3 |
| ITF - M15 St Petersburg | 2021/02/01 07:00 | Daniil Glinka v Leonid Sheyngezikht | 6-3,6-4 |
| ITF - M15 Skopje | 2021/06/06 09:00 | Ondrej Horak v Luigi Sorrentino | 6-0,1-6,11-9 |
| ITF - M15 Skopje | 2021/05/30 09:30 | Ondrej Horak v Viktor Jovic | 4-6,3-6 |
| ITF - M25 Most | 2021/05/23 14:00 | Martin Damm v Ondrej Horak | 7-5,6-4 |
| ITF - M25 Jablonec Nad Nisou | 2021/05/17 07:30 | Ondrej Horak v Tomas Papik | 1-6,4-6 |
| ITF - M25 Jablonec Nad Nisou | 2021/05/16 08:30 | George Loffhagen v Ondrej Horak | 5-7,1-6 |
| ITF M25 - Praga | 2021/05/10 08:00 | Jan Satral v Ondrej Horak | 6-1,6-2 |
| ITF M25 - Praga | 2021/05/09 10:00 | Ondrej Horak v Jan Jermar | 7-6,6-3 |
| ITF - M15 Sibenik | 2021/04/20 08:00 | Alen Rogic-Hadzalic v Ondrej Horak | 6-1,6-4 |