Round: 26 Ground: Clay
| ITF Macedonia F1 | 2016/07/05 08:30 | Gabb, Richard v Zemel, Yankel | 6-0,6-4 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Lazov, Alexander v Gabb, Richard | 7-6,6-3 |
| ITF Macedonia F2 | 2016/06/30 09:50 | Nino Serdarusic v Gabb, Richard | 3-6,3-6 |
| ITF Macedonia F2 | 2016/06/28 08:45 | Hirschmueller, Christian v Gabb, Richard | 1-6,4-6 |
| Turkey F17, Singles Qualifying | 2016/04/28 09:35 | Frigerio, Lorenzo v Gabb, Richard | 6-7,2-6 |
| Turkey F17, Singles Qualifying | 2016/04/27 08:00 | Blumenberg, Alex v Gabb, Richard | 4-6,3-6 |
| Turkey F16, Singles Qualifying | 2016/04/24 09:00 | Heyman, Christopher v Gabb, Richard | 7-6,6-0 |
| Turkey F16, Singles Qualifying | 2016/04/23 08:00 | Gabb, Richard v Dubail, Julien | 6-1,7-5 |
| ITF Macedonia F1 | 2016/07/05 08:30 | Micov, Stefan v Jotovski, Tomislav | 3-6,4-6 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Mesaros, Kristijan v Jotovski, Tomislav | 6-0,6-0 |
| ITF Macedonia F2 | 2016/06/30 10:00 | Jotovski, Tomislav v Salaba, Libor | 6-3,3-6,6-1 |
| ITF Macedonia F2 | 2016/06/28 09:25 | Gabriel Donev v Jotovski, Tomislav | 4-6,1-6 |
| ITF Macedonia F1 | 2016/06/22 14:00 | Petrovic, Danilo v Jotovski, Tomislav | 6-3,7-5 |
| ITF Bosnia and Herzegovina F3 | 2016/05/27 13:00 | Katic, Dejan v Jotovski, Tomislav | 6-1,7-5 |
| ITF Bosnia and Herzegovina F3 | 2016/05/26 13:00 | Jotovski, Tomislav v Kekez, Duje | 6-3,3-6,6-1 |
| ITF Bosnia and Herzegovina F2 | 2016/05/20 12:10 | Katic, Dejan v Jotovski, Tomislav | 4-6,6-4,7-6 |