Round: 27 Ground: Clay
| ITF Bosnia and Herzegovina F1 | 2016/05/14 08:00 | Tomislav Jotovski v Kristijan Mesaros | 5-7,0-6 |
| ITF Macedonia F2 | 2016/06/30 09:30 | Markos Kalovelonis v Kristijan Mesaros | 1-6,1-6 |
| ITF Macedonia F2 | 2016/06/29 10:10 | Filip Veger v Kristijan Mesaros | 4-6,5-7 |
| ITF Macedonia F1 | 2016/06/23 14:00 | Kristijan Mesaros v Christopher O'Connell | 7-5,5-7,0-6 |
| ITF Macedonia F1 | 2016/06/22 14:00 | Kristijan Mesaros v Besir Durguti | 6-1,6-2 |
| ITF Italy F15 | 2016/06/19 13:30 | Kristijan Mesaros v Pascal Meis | 6-1,6-2 |
| ITF Italy F15 | 2016/06/18 12:30 | Kristijan Mesaros v Markus Eriksson | 6-4,6-2 |
| ITF Italy F15 | 2016/06/17 17:05 | Kristijan Mesaros v Omar Giacalone | 7-5,6-1 |
| ITF Italy F15 | 2016/06/15 18:00 | Patricio Heras v Kristijan Mesaros | 3-6,7-6,1-6 |
| 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 Bosnia and Herzegovina F2 | 2016/05/20 12:10 | Dejan Katic v Tomislav Jotovski | 4-6,6-4,7-6 |
| ITF Bosnia and Herzegovina F2 | 2016/05/19 08:00 | Tomislav Jotovski v Danylo Kalenichenko | 6-2,2-6,7-5 |
| ITF Bosnia and Herzegovina F2 | 2016/05/17 12:05 | Caio Silva v Tomislav Jotovski | 1-6,3-6 |