| US Open 2016 | 08/31 22:05 | 24 | Sergiy Stakhovsky v Marin Čilić | 1-6,2-6,3-6 | |
| US Open | 08/29 15:00 | 23 | Sergiy Stakhovsky v Gastao Elias | 6-1,3-6,2-6,6-3,7-6 | |
| ATP - Umag | 07/19 15:00 | 25 | Andrej Martin v Sergiy Stakhovsky | 7-6,6-4 | |
| Cupa Davis | 07/17 13:30 | - | Sergiy Stakhovsky v Dennis Novak | 6-3,6-3,6-7,7-5 | |
| Cupa Davis | 07/15 10:35 | - | Sergiy Stakhovsky v Gerald Melzer | 6-3,6-4,6-3 | |
| Wimbledon | 06/30 11:40 | 24 | Marin Čilić v Sergiy Stakhovsky | 6-2,6-7,6-4,6-4 | |
| Wimbledon | 06/27 10:30 | 23 | Sergiy Stakhovsky v Yoshihito Nishioka | 6-3,6-4,6-4 | |
| ATP - Halle | 06/16 12:40 | 26 | Sergiy Stakhovsky v David Goffin | Retired | |
| ATP - Halle | 06/13 11:30 | 25 | Denis Kudla v Sergiy Stakhovsky | 5-7,6-4,3-6 | |
| ATP Halle Qual | 06/12 10:20 | 46 | Rajeev Ram v Sergiy Stakhovsky | 6-7,6-3,2-6 | |
| ATP Halle Qual | 06/11 11:55 | 45 | Yoshihito Nishioka v Sergiy Stakhovsky | 3-6,1-6 | |
| ATP - Stuttgart | 06/09 09:00 | 26 | Sergiy Stakhovsky v Mikhail Youzhny | 3-6,6-7 | |
| ATP - Stuttgart | 06/07 16:35 | 25 | Jan Choinski v Sergiy Stakhovsky | Retired | |
| ATP Stuttgart Qual | 06/06 09:00 | 46 | Sergiy Stakhovsky v Frank Moser | 6-4,6-4 | |
| ATP Stuttgart Qual | 06/04 13:55 | 45 | Sergiy Stakhovsky v Jan Mertl | 6-4,3-6,6-1 | |
| French Open Qual | 05/19 11:55 | 45 | Sergiy Stakhovsky v Marsel Ilhan | 4-6,4-6 | |
| French Open Qual | 05/17 09:25 | 44 | Sergiy Stakhovsky v Brydan Klein | 6-3,6-3 | |
| ATP - Miami | 03/26 17:05 | 24 | Jack Sock v Sergiy Stakhovsky | Retired | |
| ATP - Miami | 03/24 22:30 | 23 | Nicolas Jarry v Sergiy Stakhovsky | 6-7,5-7 | |
| Challenger - Quimper | 03/05 15:55 | 28 | Andrey Rublev v Sergiy Stakhovsky | Walkover | |
| Challenger - Quimper | 03/04 19:40 | 27 | Romain Jouan v Sergiy Stakhovsky | 4-6,7-6,1-6 | |
| Challenger - Quimper | 03/03 11:30 | 26 | Alexandre Sidorenko v Sergiy Stakhovsky | 4-6,6-7 | |
| Challenger - Quimper | 03/01 18:50 | 25 | Aslan Karatsev v Sergiy Stakhovsky | 6-7,6-7 | |
| Challenger - Orleans | 10/02 14:50 | 27 | Sergiy Stakhovsky v Jan-Lennard Struff | 4-6,2-6 | |
| Challenger - Orleans | 10/01 18:55 | 26 | Sergiy Stakhovsky v Andrey Golubev | 6-1,6-3 | |
| Challenger - Orleans | 09/29 18:00 | 25 | Sergiy Stakhovsky v Filip Veger | 6-4,6-7,6-3 | |
| US Open | 09/04 16:25 | 25 | Jo-Wilfried Tsonga v Sergiy Stakhovsky | 6-3,7-5,6-2 | |
| US Open | 09/02 20:55 | 24 | Sergiy Stakhovsky v Illya Marchenko | 6-4,7-6,4-6,6-4 | |
| US Open | 08/31 18:05 | 23 | Sergiy Stakhovsky v John Millman | 6-1,3-6,7-6,6-4 | |
| ATP - Cincinnati | 08/17 16:45 | 24 | Sergiy Stakhovsky v Bernard Tomic | 4-6,3-6 |