Round: 25 Ground: Clay
| Challenger Todi | 2016/07/04 12:15 | Antonio Massara v Cem Ilkel | 6-3,5-7,5-7 |
| Challenger Todi | 2016/07/03 14:50 | Lucas Miedler v Antonio Massara | 6-4,6-7,3-6 |
| ITF Italy F18 | 2016/07/02 12:30 | Trusendi, Walter v Antonio Massara | 6-1,6-1 |
| ITF Italy F18 | 2016/07/01 14:40 | Capecchi, Daniele v Antonio Massara | 5-7,6-3,3-6 |
| ITF Italy F18 | 2016/06/29 12:30 | Roncalli, Simone v Antonio Massara | 1-6,3-6 |
| ITF Italy F18 | 2016/06/28 10:10 | Rizzuti, Giovanni v Antonio Massara | 4-6,3-6 |
| ITF Poland F4 | 2016/06/17 09:00 | Antonio Massara v Gawron, Marcin | 4-6,0-6 |
| ITF Poland F4 | 2016/06/16 10:30 | Antonio Massara v David Poljak | 3-6,6-2,6-3 |
| ITF Italy F18 | 2016/06/27 18:45 | Andrea Guerrieri v Maccari, Federico | 3-6,3-6 |
| ITF Italy F16 | 2016/06/21 14:00 | Picco, Francesco v Andrea Guerrieri | 6-3,6-2 |
| ITF Italy F15 | 2016/06/15 11:30 | Eriksson, Markus v Andrea Guerrieri | 6-2,6-3 |
| ITF Italy F15 | 2016/06/14 10:55 | Andrea Guerrieri v Baldi, Filippo | 1-6,6-4,6-3 |
| ITF Croatia F1 | 2016/03/05 09:00 | Petrovic, Danilo v Andrea Guerrieri | 6-1,7-6 |
| ITF Croatia F1 | 2016/03/04 08:30 | Ilic, Luka v Andrea Guerrieri | 1-6,6-7 |
| ITF Croatia F1 | 2016/03/02 10:10 | Andrea Guerrieri v Bjelica, Ivan | 6-4,7-5 |
| ITF Tunisia F7 | 2016/02/25 12:20 | Andrea Guerrieri v Trusendi, Walter | 0-6,4-6 |