Round: 46 Ground: Hardcourt outdoor
| Côme, Italie, Qualifications | 2016/08/27 12:25 | Crepaldi, Erik v Andrea Collarini | 1-6,0-6 |
| Manerbio, Italie, Qualifications | 2016/08/20 15:45 | Wang, Tak Khunn v Crepaldi, Erik | 6-3,6-1 |
| Challenger Aptos | 2016/08/11 18:00 | Crepaldi, Erik v King, Evan | 3-6,5-7 |
| Challenger Aptos | 2016/08/09 00:00 | Crepaldi, Erik v Halebian, Alexios | 7-5,7-5 |
| Challenger Granby Qual | 2016/08/01 16:15 | Mcgee, James v Crepaldi, Erik | 6-1,6-4 |
| Challenger Granby Qual | 2016/07/31 16:30 | Jones, Greg v Crepaldi, Erik | 6-2,4-6,5-7 |
| Cali, Colombia | 2016/07/07 15:45 | Crepaldi, Erik v Barrientos, Nicolas | 2-6,2-6 |
| Cali, Colombia | 2016/07/05 16:30 | Crepaldi, Erik v Smith, Connor | 7-6,6-2 |
| 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 Finland F2 | 2016/08/09 09:20 | Gerini, Tomas v Gray, Jonathan | 3-6,5-7 |
| ITF Finland F2 Qual | 2016/08/07 14:35 | Gray, Jonathan v Emil Ruusuvuori | 7-6,6-0 |
| ITF Finland F2 Qual | 2016/08/06 12:30 | Gray, Jonathan v Otto Virtanen | 6-4,6-0 |
| ITF Latvia F1 | 2016/08/02 09:10 | Grigelis, Laurynas v Gray, Jonathan | 7-6,6-0 |
| ITF Estonia F1 | 2016/07/24 22:00 | Gray, Jonathan v Alexander Vasilenko | 6-2,4-6,4-6 |