Round: 27 Ground: Clay
| ITF Macedonia F1 | 2016/07/07 08:30 | Kristijan Mesaros v Francesco Garzelli | 6-2,7-5 |
| ITF Macedonia F2 | 2016/07/03 09:15 | Dimitar Grabul v Kristijan Mesaros | 7-5,1-6,7-6 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Kristijan Mesaros v Tomislav Jotovski | 6-0,6-0 |
| 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 Italia F15 | 2016/06/19 13:30 | Kristijan Mesaros v Pascal Meis | 6-1,6-2 |
| ITF Macedonia F1 | 2016/07/07 10:30 | Igor Saveljic v Ljubomir Celebic | 2-6,0-6 |
| ITF Macedonia F1 | 2016/07/06 08:30 | Besir Durguti v Ljubomir Celebic | 0-6,3-6 |
| ITF Macedonia F2 | 2016/06/30 08:00 | Christopher O'Connell v Ljubomir Celebic | 6-2,7-5 |
| ITF Macedonia F2 | 2016/06/29 12:10 | Dejan Katic v Ljubomir Celebic | 4-6,2-6 |
| ITF Macedonia F1 | 2016/06/21 07:30 | Ljubomir Celebic v Christopher O'Connell | 4-6,1-6 |
| ITF Italia F15 | 2016/06/14 12:55 | Patricio Heras v Ljubomir Celebic | 6-2,7-5 |
| ITF Italia F12 | 2016/05/24 13:45 | Laurynas Grigelis v Ljubomir Celebic | 6-2,6-4 |
| ITF Italia F32 | 2016/05/21 09:50 | Ljubomir Celebic v Riccardo Bellotti | 2-6,1-6 |