Round: 25 Ground: Hardcourt indoor
| ITF Italy F32 | 2016/05/20 08:30 | Christopher O'Connell v Tobias Simon | 7-5,7-6 |
| ITF Italy F32 | 2016/05/19 10:50 | Jonathan Mridha v Tobias Simon | 4-6,2-6 |
| ITF Italy F32 | 2016/05/17 11:05 | Tobias Simon v Tomislav Ternar | 4-6,6-1,6-1 |
| ITF Italy F32 | 2016/05/13 08:00 | Tobias Simon v Nikola Cacic | 6-4,3-6,3-6 |
| ITF Italy F32 | 2016/05/12 08:00 | Tobias Simon v Florian Fallert | 2-6,6-1,7-5 |
| ITF Italy F32 | 2016/05/11 10:00 | Tallon Griekspoor v Tobias Simon | 6-3,4-6,5-7 |
| ITF Italy F32 | 2016/05/05 11:10 | Christopher O'Connell v Tobias Simon | 6-4,3-6,6-1 |
| ITF Qatar F2 | 2016/04/12 22:00 | James Marsalek v Tobias Simon | 6-4,7-6 |
| ITF Germany F15 | 2015/10/06 09:30 | Tim Ruehl v Martins Podzus | 2-6,1-6 |
| ITF Switzerland F1 Qual | 2015/03/08 10:00 | Adam Majchrowicz v Tim Ruehl | 1-6,2-6 |
| ITF Switzerland F1 Qual | 2015/03/07 08:00 | Gabriel Currlin v Tim Ruehl | 1-6,3-6 |