Round: 25 Ground: Clay
| ITF Austria F2 | 2016/07/13 08:35 | Tobias Simon v Stefanos Tsitsipas | 6-4,2-6,2-6 |
| ITF Austria F2 | 2016/07/12 10:25 | Thales Turini v Tobias Simon | 4-6,3-6 |
| ITF Netherlands F3 | 2016/06/27 18:45 | Jelle Sels v Tobias Simon | 6-4,7-5 |
| ITF Netherlands F1 | 2016/06/14 10:55 | Mick Veldheer v Tobias Simon | 1-6,2-6 |
| ITF Romania F5 | 2016/06/11 10:00 | Roberto Marcora v Tobias Simon | 6-7,6-1,7-6 |
| ITF Romania F5 | 2016/06/10 09:00 | Thales Turini v Tobias Simon | 1-6,3-6 |
| ITF Romania F5 | 2016/06/09 07:30 | Filipp Kekercheni v Tobias Simon | 3-6,6-3,1-6 |
| ITF Romania F5 | 2016/06/07 07:00 | Tobias Simon v Fernando Romboli | 6-1,7-5 |
| ITF USA F24 | 2016/07/20 18:15 | Farris Fathi Gosea v Robbie Mudge | 6-7,2-6 |
| ITF Canada F5 | 2016/07/06 21:00 | Farris Fathi Gosea v Peter Polansky | 2-6,5-7 |
| ITF Canada F4 | 2016/06/30 17:00 | Farris Fathi Gosea v Peter Polansky | 3-6,2-6 |
| ITF Canada F4 | 2016/06/28 18:45 | Conor Berg v Farris Fathi Gosea | 6-7,4-6 |
| ITF Canada F3 | 2016/06/24 18:00 | Raymond Sarmiento v Farris Fathi Gosea | 6-4,6-3 |
| ITF Canada F3 | 2016/06/23 18:20 | Gonzales Austin v Farris Fathi Gosea | 6-4,3-6,3-6 |
| ITF Canada F3 | 2016/06/22 20:35 | Farris Fathi Gosea v Blake Mott | 6-4,2-6,7-6 |
| ITF USA F19 | 2016/06/17 18:00 | Mikael Torpegaard v Farris Fathi Gosea | 6-2,6-4 |