Round: 25 Ground: Clay
| ITF Serbia F8 Qual | 2015/08/09 08:00 | Antonio Massara v Milan Drinic | 6-3,6-4 |
| ITF Serbia F3 | 2016/08/04 11:10 | Milan Drinic v Christopher O'Connell | 3-6,6-2,0-6 |
| ITF Serbia F3 | 2016/08/03 09:45 | Milan Drinic v Igor Banicevic | 6-2,6-0 |
| ITF Serbia F2 | 2016/07/28 12:15 | Dejan Katic v Milan Drinic | 7-6,7-6 |
| ITF Serbia F2 | 2016/07/27 12:15 | Igor Banicevic v Milan Drinic | 1-6,4-6 |
| ITF Serbia F1 | 2016/07/23 08:00 | Nerman Fatic v Milan Drinic | 6-2,2-6,6-2 |
| ITF Serbia F1 | 2016/07/22 10:20 | Viktor Filipenko v Milan Drinic | 3-6,3-6 |
| ITF Serbia F1 | 2016/07/21 10:05 | Milan Drinic v Pawel Juszczak | 4-6,6-3,6-2 |
| ITF Serbia F1 | 2016/07/20 13:55 | Milan Drinic v Luca Giacomelli | 6-1,6-3 |
| ITF Serbia F3 | 2016/08/06 12:15 | Michael Linzer v Antonio Massara | 6-3,6-1 |
| ITF Serbia F3 | 2016/08/05 09:20 | Antonio Massara v Nicholas Horton | 6-3,0-6,6-1 |
| ITF Serbia F3 | 2016/08/04 08:00 | Antonio Massara v Manuel Pena Lopez | 6-3,6-1 |
| ITF Serbia F3 | 2016/08/03 11:05 | Antonio Massara v Davide Galoppini | 0-6,6-3,6-2 |
| ITF Italy F22 | 2016/07/30 16:00 | Antonio Massara v Andrea Basso | 6-7,6-3,4-6 |
| ITF Italy F22 | 2016/07/29 14:30 | Francesco Moncagatto v Antonio Massara | 5-7,5-7 |
| ITF Italy F22 | 2016/07/25 13:05 | Federico Maccari v Antonio Massara | 2-6,3-6 |
| Challenger Recanati | 2016/07/20 13:00 | Farrukh Dustov v Antonio Massara | 6-3,6-3 |