| Challenger Quimper | 01/30 10:35 | 25 | [136] Sergiy Stakhovsky v Lucas Miedler [275] | 6-7,7-6,7-6 | |
| Challenger Rennes | 01/24 13:40 | 26 | [132] Sergiy Stakhovsky v Marcos Baghdatis [122] | 4-6,6-7 | |
| Challenger Rennes | 01/22 13:30 | 25 | [132] Sergiy Stakhovsky v Evan Furness [450] | 4-6,6-3,7-6 | |
| Australian Open | 01/10 00:15 | 45 | [164] Luca Vanni v Sergiy Stakhovsky [133] | 6-4,7-6 | |
| Australian Open | 01/07 23:00 | 44 | [219] Kenny de Schepper v Sergiy Stakhovsky [133] | 3-6,6-4,3-6 | |
| ATP Doha | 01/01 12:30 | 25 | [134] Sergiy Stakhovsky v Marco Cecchinato [20] | 4-6,2-6 | |
| ATP Doha | 12/30 12:30 | 164 | [88] Mirza Basic v Sergiy Stakhovsky [135] | 6-3,2-6,3-6 | |
| ATP Doha | 12/29 10:40 | 64 | [135] Sergiy Stakhovsky v Gian Marco Moroni [215] | 7-6,7-5 | |
| ATP Doha | 12/29 09:55 | 64 | Sergiy Stakhovsky v Elias Ymer | Cancelled | |
| Challenger Andria | 11/23 16:20 | 27 | [100] Ugo Humbert v Sergiy Stakhovsky [140] | 6-0,6-4 | |
| Challenger Andria | 11/22 13:00 | 26 | Liam Caruana v Sergiy Stakhovsky | 4-6,0-6 | |
| Challenger Andria | 11/20 17:45 | 25 | [294] Matteo Viola v Sergiy Stakhovsky [140] | 1-6,5-7 | |
| Challenger Bratislava | 11/09 12:50 | 27 | [144] Sergiy Stakhovsky v Alexander Bublik [253] | 3-6,6-7 | |
| Challenger Bratislava | 11/07 17:40 | 26 | [144] Sergiy Stakhovsky v Norbert Gombos [277] | 6-7,6-4,6-2 | |
| Challenger Bratislava | 11/05 17:20 | 25 | [121] Marco Trungelliti v Sergiy Stakhovsky [144] | 2-6,4-6 | |
| Challenger Eckental | 11/01 12:00 | 26 | [178] Antoine Hoang v Sergiy Stakhovsky [146] | 6-2,6-2 | |
| Challenger Eckental | 10/31 12:15 | 25 | [296] Roberto Marcora v Sergiy Stakhovsky [146] | 4-6,4-6 | |
| Challenger Eckental | 10/30 09:00 | 25 | Stefano Travaglia v Sergiy Stakhovsky | Cancelled | |
| ATP Vienna | 10/21 11:00 | 164 | [63] Denis Kudla v Sergiy Stakhovsky [150] | 6-1,2-6,6-2 | |
| ATP Vienna | 10/20 09:00 | 64 | [150] Sergiy Stakhovsky v Bradley Klahn [102] | 6-7,6-4,6-4 | |
| ATP Antwerp | 10/16 11:20 | 25 | [32] Gilles Simon v Sergiy Stakhovsky [150] | 6-0,6-4 | |
| ATP Antwerp | 10/15 11:30 | 164 | [109] Felix Auger Aliassime v Sergiy Stakhovsky [150] | Retired | |
| ATP Antwerp | 10/14 15:00 | 64 | [191] Kenny de Schepper v Sergiy Stakhovsky [149] | 6-7,4-6 | |
| Challenger Ortisei | 10/09 17:50 | 25 | [149] Sergiy Stakhovsky v Simone Bolelli [150] | 6-7,3-6 | |
| Challenger Orleans | 09/28 16:30 | 27 | [148] Sergiy Stakhovsky v Aljaz Bedene [78] | 6-7,4-6 | |
| Challenger Orleans | 09/26 20:45 | 26 | [146] Quentin Halys v Sergiy Stakhovsky [148] | 5-7,6-3,6-7 | |
| Challenger Orleans | 09/25 12:30 | 25 | [468] Tak Khunn Wang v Sergiy Stakhovsky [148] | 5-7,6-7 | |
| ATP Metz | 09/16 14:00 | 64 | [142] Sergiy Stakhovsky v Maxime Janvier [273] | 3-6,4-6 | |
| Davis Cup | 09/15 10:00 | 27 | [142] Sergiy Stakhovsky v Joao Sousa [49] | 6-2,4-6,6-4 | |
| Davis Cup | 09/14 11:30 | 27 | [142] Sergiy Stakhovsky v Pedro Sousa [144] | 6-3,6-2 |