Round: 27 Ground: Clay
| 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 Qatar F2 | 2016/04/11 22:00 | Tobias Simon v Gonzales Austin | 6-3,6-7,7-6 |
| ITF Qatar F1 | 2016/04/04 22:00 | Tobias Simon v Milos Sekulic | 2-6,6-7 |
| ITF Bahrain F1 | 2016/04/01 11:00 | Yannick Maden v Tobias Simon | 6-4,6-4 |
| ITF Bahrain F1 | 2016/03/31 11:00 | Tobias Simon v Sam Barry | 6-1,6-4 |
| ITF Italy F32 | 2016/05/12 08:00 | Nikola Cacic v Riccardo Bellotti | 6-1,3-6,6-4 |
| ITF Hungary F2 | 2016/04/28 10:15 | Germain Gigounon v Nikola Cacic | 6-2,7-5 |
| ITF Hungary F2 | 2016/04/27 08:00 | Domagoj Biljesko v Nikola Cacic | 6-2,4-6,3-6 |
| ITF Hungary F1 | 2016/04/20 10:00 | Ivan Sabanov v Nikola Cacic | 6-4,6-2 |
| ITF Belarus F1 | 2014/10/20 10:00 | Nikola Cacic v Victor Baluda | 3-6,3-6 |
| Challenger Biella | 2014/09/09 10:50 | Julien Obry v Nikola Cacic | 6-4,3-6,6-2 |
| ITF Romania F13 | 2014/08/31 07:30 | Nikola Cacic v Frederico Ferreira Silva | 6-4,4-6,7-5 |
| ITF Romania F13 | 2014/08/30 09:10 | Nikola Cacic v Roman Jebavy | 6-4,6-0 |