Round: 54 Ground: Clay
| ITF Italy F4 Qual | 2016/04/02 09:30 | Tommaso Roggero v Jonas Trinker | 4-6,7-5,6-4 |
| ITF Austria F4 Qual | 2016/07/23 17:00 | Rudolf Molleker v Jonas Trinker | 6-4,3-6,6-2 |
| ITF Austria F3 | 2016/07/16 07:45 | Petr Hajek v Jonas Trinker | 6-4,6-2 |
| ITF Austria F2 | 2016/07/09 07:15 | Jonas Trinker v Yvo Panak | 4-6,2-6 |
| ITF Austria F1 | 2016/07/02 07:15 | Johannes Bangratz v Jonas Trinker | 7-6,6-2 |
| ITF Germany F4 | 2016/06/18 08:00 | Jonas Trinker v Lukas Ruepke | 0-6,2-6 |
| ITF Netherlands F1 Qual | 2016/06/11 08:00 | Michiel de Krom v Jonas Trinker | 6-0,4-6,6-4 |
| ITF Italy F13 | 2016/05/29 07:30 | Jonas Trinker v Filippo Mora | 4-6,6-2,3-6 |
| ITF Italy F9 | 2016/05/03 08:00 | Yannick Jankovits v Jonas Trinker | 6-0,6-1 |
| ITF Italy F22 | 2016/07/25 11:25 | Alexei Popyrin v Tommaso Roggero | 6-0,6-2 |
| ITF Italy F20 Qual | 2016/07/09 07:30 | Tommaso Roggero v Daniele Spinnato | 2-6,6-0,2-6 |
| ITF Italy F16 Qual | 2016/06/19 07:30 | Lorenzo Abbruciati v Tommaso Roggero | 6-4,6-0 |
| ITF Italy F4 Qual | 2016/04/02 09:30 | Tommaso Roggero v Jonas Trinker | 4-6,7-5,6-4 |
| ITF Italy F2 Qual | 2016/03/05 09:30 | Tommaso Roggero v Alessandro Petrone | 1-6,6-3,1-6 |