Round: 25 Ground: Clay
| ITF Finland F2 Qual | 2016/08/07 11:30 | Tomas Gerini v Jonathan Stenberg | 6-4,1-6,6-4 |
| ITF Finland F2 Qual | 2016/08/06 07:00 | Tomas Gerini v Ville-Petteri Ahti | 7-6,6-2 |
| ITF Romania F7 | 2016/06/19 10:30 | Tomas Gerini v Kento Yamada | 6-4,3-6,4-6 |
| ITF Romania F7 | 2016/06/18 10:30 | Tomas Gerini v Sergiu D Medesan | 6-0,6-3 |
| ITF Italy F9 | 2016/05/04 07:30 | Tomas Gerini v Claudio Fortuna | 5-7,1-6 |
| ITF Italy F9 | 2016/05/02 09:30 | Alexander Weis v Tomas Gerini | 3-6,5-7 |
| ITF Argentina F3 | 2016/03/15 19:10 | Tomas Gerini v Tomas Lipovsek Puches | 5-7,6-3,3-6 |
| ITF Argentina F3 | 2016/03/13 15:30 | Felipe Derdoy v Tomas Gerini | 7-6,2-6,1-6 |
| 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 Belgium F6 | 2016/07/18 10:45 | Jonathan Gray v Jules Okala | 2-6,6-7 |
| ITF Belgium F6 Qual | 2016/07/17 08:00 | Jonathan Gray v Luc Fomba | 6-2,6-3 |
| ITF Hong Kong F3 | 2016/06/18 22:00 | Jonathan Gray v Karan Rastogi | 1-6,6-7 |
| ITF Hong Kong F3 | 2016/06/17 22:00 | Xiao Gong v Jonathan Gray | 3-6,6-4,2-6 |