Round: 46 Ground: Hardcourt outdoor
| Challenger Como Qual | 2016/08/27 12:25 | Erik Crepaldi v Andrea Collarini | 1-6,0-6 |
| Challenger Manerbio Qual | 2016/08/20 15:45 | Tak Khunn Wang v Erik Crepaldi | 6-3,6-1 |
| Challenger Aptos | 2016/08/11 18:00 | Erik Crepaldi v Evan King | 3-6,5-7 |
| Challenger Aptos | 2016/08/09 00:00 | Erik Crepaldi v Alexios Halebian | 7-5,7-5 |
| Challenger Granby Qual | 2016/08/01 16:15 | James McGee v Erik Crepaldi | 6-1,6-4 |
| Challenger Granby Qual | 2016/07/31 16:30 | Greg Jones v Erik Crepaldi | 6-2,4-6,5-7 |
| Challenger Cali 2 | 2016/07/07 15:45 | Erik Crepaldi v Nicolas Barrientos | 2-6,2-6 |
| Challenger Cali 2 | 2016/07/05 16:30 | Erik Crepaldi v Connor Smith | 7-6,6-2 |
| 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 |