Round: 27 Ground: Clay
| ITF Serbia F4 | 2016/08/11 11:15 | Nikola Cacic v Goran Markovic | 3-6,6-4,6-4 |
| ITF Serbia F4 | 2016/08/10 07:30 | Nikola Cacic v Christian Hirschmueller | 2-6,7-5,6-3 |
| ITF Serbia F3 | 2016/08/02 08:00 | Nikola Cacic v Andre Biro | 1-6,5-7 |
| ATP Umag | 2016/07/20 15:30 | Nikola Cacic v Jeremy Chardy | 2-6,0-6 |
| ATP Umag | 2016/07/18 15:30 | Aljaz Bedene v Nikola Cacic | 7-5,4-6,4-6 |
| ATP Umag Qual | 2016/07/17 09:00 | Nikola Cacic v Michal Konecny | 6-3,6-2 |
| ATP Bastad Qual | 2016/07/11 09:00 | Nikola Cacic v Calvin Hemery | 1-6,2-6 |
| ATP Bastad Qual | 2016/07/10 10:00 | Milos Sekulic v Nikola Cacic | 7-6,5-7,4-6 |
| ITF Serbia F4 | 2016/08/09 09:10 | Milan Drinic v Antonio Massara | 1-6,6-3,7-6 |
| 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 |