Round: 28 Ground: Hardcourt indoor
| Wimbledon | 2016/06/30 11:40 | Marin Cilic v Sergiy Stakhovsky | 6-2,6-7,6-4,6-4 |
| Wimbledon | 2016/06/27 10:30 | Sergiy Stakhovsky v Yoshihito Nishioka | 6-3,6-4,6-4 |
| ATP Halle | 2016/06/13 11:30 | Denis Kudla v Sergiy Stakhovsky | 5-7,6-4,3-6 |
| ATP Halle Qual | 2016/06/12 10:20 | Rajeev Ram v Sergiy Stakhovsky | 6-7,6-3,2-6 |
| ATP Halle Qual | 2016/06/11 11:55 | Yoshihito Nishioka v Sergiy Stakhovsky | 3-6,1-6 |
| ATP Stuttgart | 2016/06/09 09:00 | Sergiy Stakhovsky v Mikhail Youzhny | 3-6,6-7 |
| ATP Stuttgart Qual | 2016/06/06 09:00 | Sergiy Stakhovsky v Frank Moser | 6-4,6-4 |
| ATP Stuttgart Qual | 2016/06/04 13:55 | Sergiy Stakhovsky v Jan Mertl | 6-4,3-6,6-1 |
| Challenger San Benedetto | 2016/07/12 19:35 | Kevin Krawietz v Luca Vanni | 6-4,7-6 |
| Challenger Todi | 2016/07/08 18:15 | Marco Trungelliti v Luca Vanni | 6-3,7-6 |
| Challenger Todi | 2016/07/07 19:55 | Matteo Donati v Luca Vanni | 6-0,5-7,4-6 |
| Challenger Todi | 2016/07/06 19:35 | Andrea Arnaboldi v Luca Vanni | 4-6,4-6 |
| Wimbledon Qual | 2016/06/21 14:20 | Grega Zemlja v Luca Vanni | 6-3,6-7,6-3 |
| Challenger Perugia | 2016/06/15 09:00 | Luca Vanni v Marcelo Arevalo | 5-7,6-4,2-6 |
| Challenger Vicenza | 2016/05/25 09:30 | Luca Vanni v Andrey Golubev | 5-7,4-6 |
| Challenger Vicenza | 2016/05/24 13:20 | Luca Vanni v Joao Souza | 2-6,6-4,6-4 |