Round: 26 Ground: Grass
| ATP Stuttgart Qual | 2016/06/06 09:00 | Stakhovsky, Sergiy v Moser, Frank | 6-4,6-4 |
| ATP Stuttgart Qual | 2016/06/04 13:55 | Stakhovsky, Sergiy v Mertl, Jan | 6-4,3-6,6-1 |
| French Open Qual | 2016/05/19 11:55 | Stakhovsky, Sergiy v Marsel Ilhan | 4-6,4-6 |
| French Open Qual | 2016/05/17 09:25 | Stakhovsky, Sergiy v Klein, Brydan | 6-3,6-3 |
| ATP - Miami | 2016/03/24 22:30 | Nicolas Jarry v Stakhovsky, Sergiy | 6-7,5-7 |
| Challenger - Quimper | 2016/03/04 19:40 | Jouan, Romain v Stakhovsky, Sergiy | 4-6,7-6,1-6 |
| Challenger - Quimper | 2016/03/03 11:30 | Sidorenko, Alexandre v Stakhovsky, Sergiy | 4-6,6-7 |
| Challenger - Quimper | 2016/03/01 18:50 | Aslan Karatsev v Stakhovsky, Sergiy | 6-7,6-7 |
| Stuttgart, Germany | 2016/06/07 13:20 | Youzhny, Mikhail v Lopez, Feliciano | 7-6,6-3 |
| Open de France | 2016/05/23 12:55 | Dodig, Ivan v Youzhny, Mikhail | 6-4,5-7,7-5,2-6,6-3 |
| ATP - Genève | 2016/05/16 16:00 | Youzhny, Mikhail v Steve Johnson | 3-6,5-7 |
| ATP Madrid Qual | 2016/05/01 12:05 | Pierre-Hugues Herbert v Youzhny, Mikhail | 7-5,6-1 |
| ATP Madrid Qual | 2016/04/30 16:30 | Akira Santillan v Youzhny, Mikhail | 3-6,6-7 |
| ATP - Barcelone | 2016/04/20 09:00 | Fabio Fognini v Youzhny, Mikhail | 3-6,6-0,6-1 |
| ATP - Barcelone | 2016/04/19 09:00 | Ram, Rajeev v Youzhny, Mikhail | 2-6,2-6 |
| ATP Monte Carlo Qual | 2016/04/10 09:00 | Youzhny, Mikhail v Pierre-Hugues Herbert | 6-2,6-7,4-6 |