Round: 25 Ground: Hardcourt indoor
| ITF Egypt F30 | 2016/10/26 08:00 | Gray, Jonathan v Hopkins, David | 2-6,4-6 |
| ITF Egypt F29 | 2016/10/19 11:55 | Ridout, Robbie v Gray, Jonathan | 6-3,6-3 |
| ITF Egypt F28 | 2016/10/12 14:30 | Gray, Jonathan v Andrea Vavassori | 1-6,2-6 |
| ITF Egypt F28 Qual | 2016/10/10 14:00 | Gray, Jonathan v Winkler, Georg | 6-2,6-3 |
| ITF Egypt F27 | 2016/10/06 17:35 | Hajek, Petr v Gray, Jonathan | 7-6,5-7,6-2 |
| ITF Egypt F27 | 2016/10/05 17:10 | Ahuja, Sagar v Gray, Jonathan | 0-6,0-6 |
| France F20, Singles | 2016/09/27 09:20 | Matteo Martineau v Gray, Jonathan | 2-6,6-3,6-4 |
| ITF France F19 Qual | 2016/09/17 07:00 | Portales, Nino v Gray, Jonathan | 4-6,6-3,7-5 |
| ITF Great Britain F4 | 2016/10/28 09:00 | Clayton, Scott v Yann Marti | 4-6,3-6 |
| ITF Great Britain F4 | 2016/10/27 09:00 | Clayton, Scott v Ridout, Robbie | 6-4,6-4 |
| ITF Great Britain F4 | 2016/10/25 12:35 | Clayton, Scott v Tiran Sanghera | 6-1,6-3 |
| ITF Israel F15 | 2016/10/07 09:25 | Weintraub, Amir v Clayton, Scott | 6-1,6-2 |
| ITF Israel F15 | 2016/10/06 07:00 | Yshai Oliel v Clayton, Scott | 6-7,5-7 |
| ITF Israel F15 | 2016/10/04 06:30 | Ovil, Orel v Clayton, Scott | 0-6,1-6 |
| ITF Israel F14 | 2016/09/29 09:10 | Yshai Oliel v Clayton, Scott | 6-3,6-1 |
| ITF Israel F14 | 2016/09/28 07:00 | Zemel, Yankel v Clayton, Scott | 2-6,2-6 |