Round: 25 Ground: Clay
| ITF Great Britain F2 | 2015/01/25 10:00 | Daniel Appelgren v Jonathan Gray | 6-3,7-5 |
| ITF Greece F3 | 2016/04/07 07:00 | Alex Molcan v Daniel Appelgren | 6-4,6-4 |
| ITF Greece F3 | 2016/04/05 09:35 | Daniel Hobart v Daniel Appelgren | 3-6,3-6 |
| ITF Greece F2 | 2016/03/29 13:00 | Daniel Appelgren v George Von Massow | 6-7,2-6 |
| ITF Greece F1 | 2016/03/25 08:00 | Petr Michnev v Daniel Appelgren | 7-6,6-3 |
| ITF Greece F1 | 2016/03/22 09:50 | Daniel Appelgren v Philip Orno | 6-4,6-1 |
| ITF Great Britain F3 Qual | 2016/02/14 13:00 | Daniel Appelgren v Adam Thornton-Brown | 7-6,6-2 |
| ITF Great Britain F2 | 2016/02/10 13:40 | Sam Barry v Daniel Appelgren | 6-4,7-5 |
| ITF Great Britain F1 | 2016/02/04 10:00 | Scott Griekspoor v Daniel Appelgren | 6-3,6-0 |
| ITF Tunisia F10 | 2016/03/15 08:30 | Baptiste Crepatte v Jonathan Gray | 6-3,6-3 |
| ITF Tunisia F9 | 2016/03/10 11:50 | Jonathan Gray v Alexander Zhurbin | 7-6,1-6,4-6 |
| ITF Tunisia F9 | 2016/03/09 09:45 | Cristobal S-Corvalan v Jonathan Gray | 4-6,3-6 |
| ITF Tunisia F9 | 2016/03/07 08:30 | Jonathan Gray v Maksim Malyshev | 6-4,6-4 |
| ITF Great Britain F3 Qual | 2016/02/14 13:00 | James Marsalek v Jonathan Gray | 6-1,4-6,6-4 |
| ITF Great Britain F3 Qual | 2016/02/14 09:30 | Joachim Bjerke v Jonathan Gray | 4-6,3-6 |
| ITF Tunisia F4 | 2016/02/03 08:30 | Jonathan Gray v Cheong-Eui Kim | 2-6,2-6 |
| ITF Tunisia F3 | 2016/01/25 13:00 | Jonathan Gray v Alberto Romero De Avila Senise | 6-3,5-7,1-6 |