Round: 25 Ground: Clay
| ITF Macedonia F1 | 2016/07/07 12:10 | Milan Drinic v Lenny Hampel | 5-7,1-6 |
| ITF Macedonia F1 | 2016/07/06 10:10 | Milan Drinic v Mukund Sasikumar | 6-4,6-2 |
| ITF Macedonia F1 | 2016/07/04 12:50 | Milan Drinic v Alberto Nieto | 1-6,6-1,6-4 |
| ITF Macedonia F1 | 2016/06/23 09:10 | Milan Drinic v Claudio Fortuna | 6-3,6-7,3-6 |
| ITF Macedonia F1 | 2016/06/21 08:50 | Goran Markovic v Milan Drinic | 4-6,4-6 |
| ITF Macedonia F1 Qual | 2016/06/19 14:00 | Milan Drinic v Dante Gennaro | 7-6,2-6,6-4 |
| ITF Macedonia F1 Qual | 2016/06/18 10:00 | Milan Drinic v Thomas Does | 6-0,6-4 |
| ITF Bosnia and Herzegovina F2 | 2016/05/20 09:00 | David Pichler v Milan Drinic | 6-4,7-5 |
| ITF Austria F2 | 2016/07/10 08:00 | Mick Veldheer v Luca Giacomelli | 6-3,6-4 |
| ITF Austria F2 | 2016/07/09 07:15 | Erwin Troebinger v Luca Giacomelli | 6-7,1-6 |
| ITF Turkey F15 | 2016/04/10 08:00 | Luca Giacomelli v Daisuke Sumizawa | 6-7,3-6 |
| ITF Turkey F14 | 2016/04/04 07:00 | Franjo Raspudic v Luca Giacomelli | 6-0,6-2 |
| ITF Turkey F14 | 2016/04/03 06:30 | Sagar Ahuja v Luca Giacomelli | 3-6,5-7 |
| ITF Turkey F14 | 2016/04/02 06:30 | Savva Polukhin v Luca Giacomelli | 3-6,4-6 |
| ITF Switzerland F2 Qual | 2016/02/14 08:00 | Robin Kern v Luca Giacomelli | 6-4,6-2 |
| ITF Switzerland F1 Qual | 2016/02/07 08:00 | Lorenzo Frigerio v Luca Giacomelli | 6-3,7-5 |