Round: 25 Ground: Hardcourt outdoor
| ITF Portugal F9 | 2016/07/18 12:30 | Benjamin Hannestad v Luke Oakley | 6-3,6-7,6-2 |
| ITF Portugal F9 | 2016/07/17 09:30 | Jorge Blanco Guadalupe v Luke Oakley | 7-6,4-6,3-6 |
| ITF Portugal F9 | 2016/07/16 12:30 | Carlos Fernandez-Espinar v Luke Oakley | 3-6,4-6 |
| ITF Poland F4 Qual | 2016/06/13 08:00 | Gabriel Petit v Luke Oakley | 6-2,7-6 |
| ITF Poland F4 Qual | 2016/06/12 08:00 | Luke Oakley v Peter Bothwell | 7-6,6-2 |
| ITF Poland F4 Qual | 2016/06/11 08:00 | Samuel Bothwell v Luke Oakley | 6-7,4-6 |
| ITF Poland F3 | 2016/06/06 10:15 | Luke Oakley v Grzegorz Panfil | 3-6,4-6 |
| ITF Poland F3 Qual | 2016/06/05 08:00 | Eero Vasa v Luke Oakley | 6-7,1-6 |
| ITF Portugal F9 | 2016/07/21 12:00 | Richard Gabb v Nuno Borges | 6-1,3-6,2-6 |
| ITF Portugal F9 | 2016/07/19 08:30 | Richard Gabb v Maxime Petel | 6-3,6-3 |
| ITF Macedonia F1 | 2016/07/09 10:45 | Richard Gabb v Kristijan Mesaros | 6-4,3-6,2-6 |
| 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 |