Stadion: Court 3 Round: 26 Ground: Clay
| ITF - M15 - Bratislava | 2021/08/24 10:00 | Vasil Kirkov v Diego F Flores | 6-3,6-3 |
| ITF - M15 - Bratislava | 2021/08/20 08:00 | Vasil Kirkov v Fabian Marozsan | 6-4,1-6,4-6 |
| ITF - M15 - Bratislava | 2021/08/19 10:25 | Marat Sharipov v Vasil Kirkov | 4-6,6-7 |
| ITF - M15 - Bratislava | 2021/08/18 09:35 | Vasil Kirkov v Franco Roncadelli | 5-7,6-2,6-2 |
| ITF - M15 - Frederiksberg | 2021/08/06 10:50 | Markus Eriksson v Vasil Kirkov | 6-4,6-3 |
| ITF - M15 - Frederiksberg | 2021/08/05 08:00 | Sandro Kopp v Vasil Kirkov | 6-4,3-6,1-6 |
| ITF - M15 - Frederiksberg | 2021/08/04 08:00 | Marius Ruzgas v Vasil Kirkov | 2-6,2-6 |
| ITF - M15 - Vejle | 2021/07/30 07:55 | Karl Friberg v Vasil Kirkov | 6-2,7-6 |
| ITF - M15 - Bratislava | 2021/08/25 11:35 | Simon Freund v Obrad Markovski | 6-3,6-4 |
| ITF - M25 - Den Haag | 2021/06/27 08:00 | Simon Freund v Lodewijk Weststrate | 1-6,3-6 |
| ITF - M25 - Alkmaar | 2021/06/23 09:00 | Simon Freund v Javier Barranco Cosano | 2-6,6-7 |
| ITF - M25 - Alkmaar | 2021/06/21 14:30 | Simon Freund v Tom Pisane | 6-0,6-1 |
| ITF - M25 - Alkmaar | 2021/06/20 13:30 | Simon Freund v Buvaysar Gadamauri | 6-2,7-5 |
| ITF - M15 - Helsinki | 2021/06/02 08:10 | Simon Freund v Sean Cuenin | 2-6,6-4,4-6 |
| ITF - M15 - Jerusalem | 2021/05/12 07:00 | Yshai Oliel v Simon Freund | 6-0,7-5 |
| ITF - M15 - Ramat Hasharon | 2021/05/06 07:00 | Simon Freund v Ben Patael | 5-7,1-6 |