Round: 28 Ground: Clay
| ITF Macedonia F2 | 2016/07/01 14:30 | Christopher O'Connell v Dimitar Grabul | 6-7,6-7 |
| ITF Macedonia F2 | 2016/06/30 13:30 | Dimitar Grabul v Lenny Hampel | 6-0,4-6,6-1 |
| ITF Macedonia F2 | 2016/06/29 13:05 | Dimitar Grabul v Duje Kekez | 6-3,7-6 |
| Copa Davis | 2016/03/05 15:20 | Dimitar Grabul v Rrezart Cungu | 6-2,6-0 |
| Copa Davis | 2016/03/02 14:00 | Dimitar Grabul v Mikayel Khachatryan | 6-4,6-0 |
| ITF Suiza F1 | 2016/02/10 11:15 | Dimitar Grabul v Yann Marti | 5-7,0-6 |
| ITF Suiza F1 | 2016/02/09 14:15 | Pablo Vivero Gonzalez v Dimitar Grabul | 6-4,3-6,4-6 |
| ITF Suiza F1 - Clasificación | 2016/02/07 10:00 | Dominik Boehler v Dimitar Grabul | 6-4,2-6,4-6 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Kristijan Mesaros v Tomislav Jotovski | 6-0,6-0 |
| ITF Macedonia F2 | 2016/06/30 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 Italia F15 | 2016/06/18 12:30 | Kristijan Mesaros v Markus Eriksson | 6-4,6-2 |
| ITF Italia F15 | 2016/06/17 17:05 | Kristijan Mesaros v Omar Giacalone | 7-5,6-1 |