Round: 25 Ground: Clay
| ITF Macedonia F1 | 2016/07/07 10:45 | Richard Gabb v Tomislav Jotovski | 6-3,6-4 |
| ITF Macedonia F1 | 2016/07/05 08:30 | Stefan Micov v Tomislav Jotovski | 3-6,4-6 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Kristijan Mesaros v Tomislav Jotovski | 6-0,6-0 |
| ITF Macedonia F2 | 2016/06/30 10:00 | Tomislav Jotovski v Libor Salaba | 6-3,3-6,6-1 |
| ITF Macedonia F2 | 2016/06/28 09:25 | Gabriel Donev v Tomislav Jotovski | 4-6,1-6 |
| ITF Macedonia F1 | 2016/06/22 14:00 | Danilo Petrovic v Tomislav Jotovski | 6-3,7-5 |
| ITF Bosnia and Herzegovina F3 | 2016/05/27 13:00 | Dejan Katic v Tomislav Jotovski | 6-1,7-5 |
| ITF Bosnia and Herzegovina F3 | 2016/05/26 13:00 | Tomislav Jotovski v Duje Kekez | 6-3,3-6,6-1 |
| ITF Russia F3 | 2016/07/05 07:00 | Shalva Dzhanashia v Timur Kiyamov | 4-6,6-4,6-1 |
| ITF Russia F2 | 2016/06/29 10:05 | Timur Kiyamov v Evgeny Karlovskiy | 1-6,3-6 |
| ITF Russia F2 | 2016/06/28 07:00 | Yan Sabanin v Timur Kiyamov | 7-6,3-6,5-7 |
| ITF Italy F15 | 2016/06/14 12:50 | Timur Kiyamov v Joao Domingues | 6-7,1-6 |
| ITF Italy F15 | 2016/06/12 07:00 | Timur Kiyamov v Nicolo Turchetti | 3-6,6-0,6-4 |
| ITF Italy F15 | 2016/06/11 07:30 | Timur Kiyamov v Daniele Spinnato | 6-3,6-4 |
| ITF Qatar F3 | 2016/04/18 22:00 | Timur Kiyamov v Antoine Escoffier | 4-6,3-6 |
| ITF Qatar F2 Qual | 2016/04/09 22:00 | Timur Kiyamov v Aryan Goveas | 6-7,2-6 |