Round: 28 Ground: Clay
| ITF Macedonia F1 | 2016/07/08 08:30 | Richard Gabb v Neil Pauffley | 6-2,6-0 |
| 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 | 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 Macedonia F1 | 2016/07/08 10:05 | Kristijan Mesaros v Ljubomir Celebic | 6-3,6-1 |
| ITF Macedonia F1 | 2016/07/07 08:30 | Kristijan Mesaros v Francesco Garzelli | 6-2,7-5 |
| ITF Macedonia F2 | 2016/07/03 09:15 | Dimitar Grabul v Kristijan Mesaros | 7-5,1-6,7-6 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Kristijan Mesaros v Tomislav Jotovski | 6-0,6-0 |
| ITF Macedonia F2 | 2016/06/30 09:30 | Markos Kalovelonis v Kristijan Mesaros | 1-6,1-6 |
| ITF Macedonia F2 | 2016/06/29 10:10 | Filip Veger v Kristijan Mesaros | 4-6,5-7 |
| ITF Macedonia F1 | 2016/06/23 14:00 | Kristijan Mesaros v Christopher O'Connell | 7-5,5-7,0-6 |
| ITF Macedonia F1 | 2016/06/22 14:00 | Kristijan Mesaros v Besir Durguti | 6-1,6-2 |