Stadium: Court 1 Round: 44 Ground: Clay
| 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 Doboj | 2021/07/17 09:55 | Zsombor Piros v Dusan Obradovic | 6-1,6-3 |
| ITF M15 Pirot | 2021/09/19 07:00 | Luca Castagnola v Pavle Daljev | 6-4,6-1 |
| ITF M15 Bad Waltersdorf | 2021/08/31 08:20 | Leonardo Taddia v Luca Castagnola | 6-2,4-6,10-6 |
| ITF M15 Bad Waltersdorf | 2021/08/30 09:00 | Kaj Quirijns v Luca Castagnola | 2-6,4-6 |
| ITF M15 Bad Waltersdorf | 2021/08/22 07:00 | Niklas Rohrer v Luca Castagnola | 6-7,6-2,10-7 |
| ITF M15 Pescara | 2021/08/15 11:30 | Luca Castagnola v Alessandro Ragazzi | 2-6,7-5,10-12 |
| ITF M25 Bolzano | 2021/08/03 16:20 | Marco Bortolotti v Luca Castagnola | 6-1,3-6,6-2 |
| ITF M25 Bolzano | 2021/08/02 13:15 | Igor Solomatin v Luca Castagnola | 6-7,2-6 |
| ITF M25 Bolzano | 2021/08/02 07:00 | Nicolo Pozzani v Luca Castagnola | 4-6,6-2,8-10 |