Round: 44 Ground: Clay
| ITF M15 Antalya | 2019/10/28 07:00 | Kalin Ivanovski v Tomislav Jotovski | 6-4,3-6,7-10 |
| ITF M15 Antalya | 2019/10/28 07:00 | Kalin Ivanovski v Tomislav Jotovski | 6-4,3-6,7-10 |
| ITF M15 Antalya | 2019/10/27 07:00 | Benedikt Emesz v Kalin Ivanovski | 6-7,7-6,4-10 |
| ITF M15 Antalya | 2019/10/29 07:00 | Tomas Liska v Tomislav Jotovski | 6-1,6-3 |
| ITF M15 Antalya | 2019/10/28 07:00 | Kalin Ivanovski v Tomislav Jotovski | 6-4,3-6,7-10 |
| ITF M15 Antalya | 2019/10/27 07:00 | Mert Arabaci v Tomislav Jotovski | 0-6,0-6 |
| ITF M15 Burgas | 2019/10/11 08:00 | Tomislav Jotovski v Alexandar Lazarov | 5-7,5-7 |
| ITF M15 Burgas | 2019/10/10 07:00 | Tomislav Jotovski v Piotr Grynkowski | 6-4,6-2 |
| ITF M15 Burgas | 2019/10/08 12:00 | Tomislav Jotovski v Ivan Mikhaylyuk | 6-3,6-2 |
| ITF M15 Burgas | 2019/10/07 07:00 | Tomislav Jotovski v Mihaita Daniel Damian | 6-1,6-1 |
| ITF M15 Burgas | 2019/10/06 08:00 | Tomislav Jotovski v Zvonimir Oreskovic | 6-1,6-1 |