Round: 54 Ground: Hardcourt outdoor
| 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 |
| Challenger St Remy Qual | 2016/09/04 08:00 | Crepaldi, Erik v Gray, Jonathan | 6-4,4-6,6-3 |
| ITF Belgium F12 | 2016/08/29 10:00 | Vliegen, Joran v Gray, Jonathan | 6-1,7-5 |
| ITF Finland F3 | 2016/08/15 22:00 | Appelgren, Daniel v Gray, Jonathan | 6-1,6-2 |
| ITF Finland F2 | 2016/08/10 08:00 | Gray, Jonathan v Tallon Griekspoor | 2-6,2-6 |
| ITF Egypt F28 Qual | 2016/10/09 14:30 | Winkler, Georg v Suyal, Dinesh Chandra | 6-0,6-0 |
| ITF Egypt F27 | 2016/10/04 16:00 | Grimolizzi, Gaston-Arturo v Winkler, Georg | 6-1,6-1 |
| Egypt F27, Singles Qualifying | 2016/10/03 18:10 | Grimolizzi, Adrian Esteban v Winkler, Georg | 4-6,3-6 |
| ITF Italy F24 Qual | 2016/08/06 11:05 | Wilson Leite v Winkler, Georg | 6-2,6-0 |
| ITF Turkey F47 | 2015/11/07 08:00 | Rieder, Horst v Winkler, Georg | 3-6,3-6 |
| ITF Turkey F44 | 2015/10/31 07:30 | Winkler, Georg v Szintai, David | 4-6,2-6 |
| ITF Italy F22 Qual | 2015/08/08 13:55 | Gomez, Lucas v Winkler, Georg | 5-7,6-2,6-4 |
| ITF Italy F21 Qual | 2015/08/02 11:55 | Antonio Massara v Winkler, Georg | 6-3,6-0 |