Stadium: Court 4 Round: 44 Ground: Clay
| ITF M15 Pirot | 2021/09/20 08:00 | Dusan Obradovic v Luca Castagnola | 3-6,5-7 |
| ITF M15 Pirot | 2021/09/20 08:00 | Dusan Obradovic v Luca Castagnola | 3-6,5-7 |
| ITF M15 Zlatibor | 2021/09/13 08:00 | Dusan Obradovic v Jasza Szajrych | 5-7,3-6 |
| ITF M15 Ulcinj | 2021/08/30 11:30 | Dusan Obradovic v Dusan Rajic | 4-6,6-3,2-10 |
| ITF M15 Ulcinj | 2021/08/30 07:30 | Dusan Obradovic v Stefan Vujic | 3-6,6-3,10-7 |
| ITF M15 Novi Sad | 2021/08/03 10:05 | Charles Broom v Dusan Obradovic | 6-4,6-2 |
| ITF M15 Novi Sad | 2021/08/02 12:30 | Aleksa Pisaric v Dusan Obradovic | 2-6,2-6 |
| ITF M15 Novi Sad | 2021/08/01 12:15 | Luka Vukovic v Dusan Obradovic | 1-6,7-6,11-13 |
| ITF M15 Novi Sad | 2021/07/25 08:15 | Tomas Jirousek v Dusan Obradovic | 6-4,7-5 |
| ITF M15 Platja D'Aro | 2021/10/03 09:30 | Max Houkes v Luca Castagnola | 6-4,6-1 |
| ITF M25 Skopje | 2021/09/29 10:30 | Luca Castagnola v Matteo Arnaldi | 2-6,3-6 |
| ITF M25 Skopje | 2021/09/28 09:20 | Luca Castagnola v Sabit Suntic | 6-2,6-3 |
| ITF M25 Skopje | 2021/09/27 12:40 | Tomislav Jotovski v Luca Castagnola | 0-6,4-6 |
| ITF M15 Pirot | 2021/09/22 09:30 | Luca Castagnola v Dominik Palan | 0-6,2-6 |
| ITF M15 Pirot | 2021/09/21 09:15 | Luca Castagnola v Dusan Rajic | 7-6,6-1 |
| ITF M15 Pirot | 2021/09/20 08:00 | Dusan Obradovic v Luca Castagnola | 3-6,5-7 |
| ITF M15 Pirot | 2021/09/19 07:00 | Luca Castagnola v Pavle Daljev | 6-4,6-1 |