Round: 28 Ground: Clay
| Challenger Rome | 2016/05/05 13:15 | Marco Trungelliti v Filippo Volandri | 4-6,1-6 |
| Challenger Rome | 2016/05/04 14:25 | Filippo Volandri v Marius Copil | 7-5,6-4 |
| Challenger Rome | 2016/05/02 13:55 | Zhe Li v Filippo Volandri | 2-6,0-6 |
| Challenger Szczecin | 2015/09/17 13:25 | Filippo Volandri v Nicolas Almagro | 6-4,5-7,1-6 |
| Challenger Szczecin | 2015/09/15 14:50 | Marcin Gawron v Filippo Volandri | 3-6,5-7 |
| Challenger Genova | 2015/09/10 13:00 | Paolo Lorenzi v Filippo Volandri | 2-6,5-7 |
| Challenger Genova | 2015/09/09 15:10 | Andrea Arnaboldi v Filippo Volandri | 2-6,6-1,3-6 |
| Challenger Como | 2015/09/01 15:50 | Andrej Martin v Filippo Volandri | 7-5,6-3 |
| Challenger Rome | 2016/05/05 11:30 | Blaz Rola v Kyle Edmund | 4-6,6-3,0-6 |
| Challenger Rome | 2016/05/04 12:45 | Kevin Krawietz v Kyle Edmund | 3-6,4-6 |
| Challenger Rome | 2016/05/02 12:30 | Jurgen Zopp v Kyle Edmund | 4-6,3-6 |
| ATP Miami | 2016/03/26 00:00 | Novak Djokovic v Kyle Edmund | 6-3,6-3 |
| ATP Miami | 2016/03/23 15:00 | Kyle Edmund v Jiri Vesely | 6-4,5-7,7-6 |
| Challenger Dallas | 2016/02/07 02:20 | Daniel Evans v Kyle Edmund | 3-6,2-6 |
| Challenger Dallas | 2016/02/06 02:25 | Tim Smyczek v Kyle Edmund | 5-7,3-6 |
| Challenger Dallas | 2016/02/04 17:30 | Grega Zemlja v Kyle Edmund | 5-7,1-6 |