Round: 25 Ground: Clay
| Challenger Cortina | 2016/08/06 09:10 | Matteo Donati v Joao Souza | 6-4,6-7,4-6 |
| Challenger Cortina | 2016/08/04 13:55 | Aslan Karatsev v Matteo Donati | 6-3,6-7,4-6 |
| Challenger Cortina | 2016/08/02 10:50 | Francisco Bahamonde v Matteo Donati | 0-6,2-6 |
| Challenger Biella | 2016/07/28 10:00 | Matteo Donati v Dusan Lajovic | 6-4,5-7,3-6 |
| Challenger Biella | 2016/07/26 16:00 | Matteo Donati v Hans Podlipnik-Castillo | 6-3,6-4 |
| ATP Kitzbuhel Qual | 2016/07/17 12:25 | Daniel Gimeno-Traver v Matteo Donati | 6-2,3-6,6-3 |
| ATP Kitzbuhel Qual | 2016/07/16 14:30 | Matthias Bachinger v Matteo Donati | 7-6,2-6,2-6 |
| Challenger San Benedetto | 2016/07/11 20:05 | Matteo Donati v Constant Lestienne | 4-6,3-6 |
| Challenger Cortina | 2016/08/04 12:00 | Filippo Volandri v Laslo Djere | 5-7,4-6 |
| Challenger Cortina | 2016/08/02 15:00 | Carlos Berlocq v Filippo Volandri | 4-6,2-6 |
| Challenger Biella | 2016/07/26 14:00 | Paolo Lorenzi v Filippo Volandri | 6-0,3-6,6-1 |
| ATP Kitzbuhel | 2016/07/18 10:30 | Karen Khachanov v Filippo Volandri | 6-2,6-4 |
| ATP Kitzbuhel Qual | 2016/07/17 10:30 | Guido Andreozzi v Filippo Volandri | 6-0,2-6,3-6 |
| ATP Kitzbuhel Qual | 2016/07/16 09:00 | Nils Langer v Filippo Volandri | 1-6,6-2,6-7 |
| Challenger Milan Qual | 2016/06/23 16:35 | Daniel Gimeno-Traver v Filippo Volandri | 6-2,2-6,6-0 |
| Challenger Milan Qual | 2016/06/21 15:35 | Filippo Volandri v Lorenzo Sonego | 6-3,6-3 |