Round: 44 Ground: Clay
| ITF Italy F11 Qual | 2016/05/16 09:45 | Hunter Callahan v Alessandro Cortegiani | 6-4,6-0 |
| Challenger Rome Qual | 2016/04/30 11:35 | Marton Fucsovics v Hunter Callahan | 6-1,6-3 |
| Challenger Rome Qual | 2016/04/30 09:00 | Lorenzo Camilli v Hunter Callahan | 0-6,0-6 |
| ITF Greece F6 | 2016/04/27 07:00 | Aaron Addison v Hunter Callahan | 6-4,7-6 |
| ITF Greece F6 | 2016/04/25 09:15 | Hunter Callahan v Pavel Krainik | 3-6,7-5,6-3 |
| ITF Greece F5 | 2016/04/21 10:15 | Hunter Callahan v Lloyd Glasspool | 6-7,2-6 |
| ITF Greece F5 | 2016/04/20 10:10 | Hunter Callahan v Raymond Sarmiento | 4-6,7-6,7-5 |
| ITF Greece F5 | 2016/04/18 08:40 | Martin Beran v Hunter Callahan | 6-3,3-6,6-7 |
| ITF Italy F11 Qual | 2016/05/16 08:55 | Pasquale De Giorgio v Luca Tomasetto | 2-6,0-6 |
| ITF Italy F10 | 2016/05/11 10:40 | Cristian Carli v Luca Tomasetto | 6-0,7-6 |
| ITF Italy F10 | 2016/05/10 13:40 | Luca Tomasetto v Erik Crepaldi | 6-3,6-3 |
| ITF Italy F4 | 2016/04/05 10:55 | Luca Tomasetto v Andrea Vavassori | 6-7,6-7 |
| ITF Italy F2 Qual | 2016/03/05 09:30 | Luca Tomasetto v Fabrizio Ornago | 4-6,2-6 |
| ITF Italy F33 | 2015/10/27 09:45 | Marco Bortolotti v Luca Tomasetto | 6-4,6-4 |
| ITF Italy F33 Qual | 2015/10/25 08:00 | Luca Tomasetto v Davide Albertoni | 6-4,6-0 |
| ITF Italy F32 Qual | 2015/10/17 10:30 | Luca Tomasetto v Ettore Capello | 4-6,5-7 |