Round: 26 Ground: Clay
| ITF Serbia F1 | 2016/07/20 10:30 | Tomislav Jotovski v Timur Kiyamov | 6-2,6-2 |
| ITF Macedonia F1 | 2016/07/07 10:45 | Richard Gabb v Tomislav Jotovski | 6-3,6-4 |
| ITF Macedonia F1 | 2016/07/05 08:30 | Stefan Micov v Tomislav Jotovski | 3-6,4-6 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Kristijan Mesaros v Tomislav Jotovski | 6-0,6-0 |
| ITF Macedonia F2 | 2016/06/30 10:00 | Tomislav Jotovski v Libor Salaba | 6-3,3-6,6-1 |
| ITF Macedonia F2 | 2016/06/28 09:25 | Gabriel Donev v Tomislav Jotovski | 4-6,1-6 |
| ITF Macedonia F1 | 2016/06/22 14:00 | Danilo Petrovic v Tomislav Jotovski | 6-3,7-5 |
| ITF Bosnia and Herzegovina F3 | 2016/05/27 13:00 | Dejan Katic v Tomislav Jotovski | 6-1,7-5 |
| ITF Serbia F1 | 2016/07/20 07:30 | Manuel Pena Lopez v Duje Kekez | 7-6,6-2 |
| ITF Serbia F1 Qual | 2016/07/19 08:00 | Manuel Pena Lopez v Darko Bojanovic | 6-3,7-6 |
| ITF Serbia F1 Qual | 2016/07/16 10:00 | Manuel Pena Lopez v Igor Saveljic | 6-3,6-4 |
| ITF Germany F6 | 2016/07/07 10:00 | Manuel Pena Lopez v Jakob Sude | 6-7,3-6 |
| ITF Germany F6 | 2016/07/04 10:00 | Manuel Pena Lopez v Tristan Meraut | 6-2,6-2 |
| ITF Germany F6 | 2016/07/03 12:00 | Manuel Pena Lopez v Christophe Tholl | 6-4,6-1 |
| Challenger Marburg | 2016/06/27 12:00 | Nicolas Kicker v Manuel Pena Lopez | 6-7,6-3,6-3 |
| ATP Geneva Qual | 2016/05/14 09:00 | Evgeny Donskoy v Manuel Pena Lopez | 7-6,6-3 |