Stadium: Court 5 Round: 62 Ground: Clay
| ITF M15 Pirot | 2021/09/24 09:40 | Tomislav Jotovski v Andrey Chepelev | 2-6,2-6 |
| ITF M15 Pirot | 2021/09/23 11:00 | Aleksandar Tomas v Tomislav Jotovski | 3-6,1-6 |
| ITF M15 Zlatibor | 2021/09/14 11:10 | Tomislav Jotovski v Veljko Krstic | 4-6,1-6 |
| ITF M15 Ulcinj | 2021/09/06 13:00 | Gabriele Piraino v Tomislav Jotovski | 6-3,6-0 |
| ITF M15 Ulcinj | 2021/09/05 07:30 | Alan Postay v Tomislav Jotovski | 3-6,4-6 |
| ITF M15 Ulcinj | 2021/09/01 10:40 | Tomislav Jotovski v Rrezart Cungu | 0-6,6-4,1-6 |
| ITF M15 Ulcinj | 2021/08/30 13:00 | Tomislav Jotovski v Felipe Derdoy | 6-1,6-2 |
| ITF M15 Ulcinj | 2021/08/30 07:30 | Tomislav Jotovski v Petar Jovanovic | 6-4,6-3 |
| 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 |
| 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 |