Round: 25 Ground: Clay
| ITF Italy F22 | 2016/07/25 13:05 | Federico Maccari v Antonio Massara | 2-6,3-6 |
| ITF Italy F21 Qual | 2016/07/16 10:30 | Federico Maccari v Marco Miceli | 4-6,6-7 |
| ITF Italy F18 | 2016/06/29 14:20 | Francesco Picco v Federico Maccari | 7-5,7-6 |
| ITF Italy F18 | 2016/06/27 18:45 | Andrea Guerrieri v Federico Maccari | 3-6,3-6 |
| ITF Italy F16 Qual | 2016/06/18 08:00 | Federico Maccari v Lorenzo Abbruciati | 3-6,5-7 |
| ITF Italy F15 | 2016/06/12 07:00 | Federico Maccari v Blake Ellis | 6-4,1-6,4-6 |
| ITF Italy F15 | 2016/06/11 07:30 | Federico Maccari v Daniele Chiurulli | 3-6,6-3,7-6 |
| ITF Italy F14 Qual | 2016/06/05 08:00 | Federico Maccari v Nicolo Turchetti | 3-6,6-2,3-6 |
| ITF Italy F25 Qual | 2016/08/15 10:20 | Kirill Kivattsev v Ludovico Scerrati | 6-1,6-2 |
| ITF Austria F5 | 2016/08/09 16:05 | Philipp Schroll v Kirill Kivattsev | 6-7,7-6,6-4 |
| ITF Austria F5 Qual | 2016/08/08 08:00 | Kirill Kivattsev v Thomas Jan Dafcik | 6-3,2-6,6-1 |
| ITF Austria F5 Qual | 2016/08/07 08:30 | Kirill Kivattsev v Patric Prinoth | 6-3,6-2 |
| Challenger Cortina Qual | 2016/07/30 12:55 | Kirill Kivattsev v Nicolas Jarry | 2-6,2-6 |
| ITF Bosnia and Herzegovina F2 | 2016/05/17 10:00 | Dejan Katic v Kirill Kivattsev | 7-5,6-2 |
| ITF Bosnia and Herzegovina F2 Qual | 2016/05/16 08:00 | Kirill Kivattsev v Daniel Orlita | 6-2,6-2 |
| ITF Bosnia and Herzegovina F2 Qual | 2016/05/15 08:00 | Kirill Kivattsev v Feda Bilic | 6-3,6-0 |