Stadium: Court 9 Round: 62 Ground: Clay
| ITF M15 Heraklion | 2021/11/29 10:00 | Jan Kupcic v Radu F Macovei | 6-4,1-6,4-10 |
| ITF M15 Heraklion | 2021/11/23 07:00 | Aristotelis Thanos v Jan Kupcic | 6-0,6-2 |
| ITF M15 Heraklion | 2021/11/22 11:00 | Jan Kupcic v Sean Hodkin | 7-6,0-6,10-8 |
| ITF M15 Bad Waltersdorf | 2021/08/29 07:00 | Jan Kupcic v Alberto Morolli | 6-1,3-6,8-10 |
| ITF M25 Kiseljak | 2021/05/24 12:15 | Jan Kupcic v Rrezart Cungu | 6-4,0-6,4-10 |
| ITF M25 Kiseljak | 2021/05/23 10:45 | Jan Kupcic v Max Van Wijk | 2-6,0-6 |
| ITF M15 Sibenik | 2021/05/17 11:00 | Jan Kupcic v Taiyo Yamanaka | 5-7,6-0,4-10 |
| ITF M15 Sibenik | 2021/05/16 07:30 | Benedikt Emesz v Jan Kupcic | 1-6,6-4,6-10 |
| ITF M15 Sozopol | 2021/10/10 13:30 | Matic Dimic v George Lazarov | 7-5,6-0 |
| ITF M15 Sozopol | 2021/10/06 06:45 | Yan Bondarevskiy v George Lazarov | 6-7,6-1,6-3 |
| ITF M15 Sozopol | 2021/10/05 06:30 | George Lazarov v Nikola Keremedchiev | 6-2,6-7,3-10 |
| ITF M15 Sozopol | 2021/10/04 08:00 | George Lazarov v Dan Radu Munteanu | 6-0,6-2 |
| ITF M15 Sozopol | 2021/09/16 07:00 | Petru-Alexandru Luncanu v George Lazarov | 6-1,1-6,7-6 |
| ITF M15 Sozopol | 2021/09/15 08:30 | George Lazarov v Gabriel Donev | 6-1,6-3 |
| ITF M15 Sozopol | 2021/09/14 07:00 | George Lazarov v Mikhail Minakov | 7-5,4-6,10-4 |
| ITF M15 Sozopol | 2021/09/13 08:00 | Luigi Castelletti v George Lazarov | 3-6,4-6 |