Round: 25 Ground: Hardcourt indoor
| ITF Belgium F12 | 2016/08/29 10:00 | Joran Vliegen v Jonathan Gray | 6-1,7-5 |
| ITF Finland F3 | 2016/08/15 22:00 | Daniel Appelgren v Jonathan Gray | 6-1,6-2 |
| ITF Finland F2 | 2016/08/10 08:00 | Jonathan Gray v Tallon Griekspoor | 2-6,2-6 |
| ITF Finland F2 | 2016/08/09 09:20 | Tomas Gerini v Jonathan Gray | 3-6,5-7 |
| ITF Finland F2 Qual | 2016/08/07 14:35 | Jonathan Gray v Emil Ruusuvuori | 7-6,6-0 |
| ITF Finland F2 Qual | 2016/08/06 12:30 | Jonathan Gray v Otto Virtanen | 6-4,6-0 |
| ITF Latvia F1 | 2016/08/02 09:10 | Laurynas Grigelis v Jonathan Gray | 7-6,6-0 |
| ITF Estonia F1 | 2016/07/24 22:00 | Jonathan Gray v Alexander Vasilenko | 6-2,4-6,4-6 |
| ITF Portugal F10 | 2016/07/27 16:00 | Fran Zvonimir Zgombic v Scott Clayton | 6-4,7-5 |
| ITF Portugal F9 | 2016/07/21 08:30 | Scott Clayton v Alon Elia | 5-7,6-3,6-7 |
| ITF Portugal F9 | 2016/07/20 08:30 | Scott Clayton v Sergi Fontcuberta | 7-5,6-2 |
| ITF Turkey F24 | 2016/06/15 12:40 | Scott Clayton v Alexander Babanine | 4-6,6-1,3-6 |
| ITF Turkey F23 MD | 2016/06/09 09:00 | Scott Clayton v Nicolaas Scholtz | 6-3,1-6,6-7 |
| ITF Turkey F23 MD | 2016/06/08 12:45 | Alex Blumenberg v Scott Clayton | 0-6,7-6,3-6 |
| ITF Portugal F6 | 2016/05/20 13:05 | Joao Domingues v Scott Clayton | 6-1,6-2 |
| ITF Portugal F6 | 2016/05/19 11:00 | Scott Clayton v Mick Lescure | 6-1,7-5 |