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