| ATP Antwerp | 10/13 09:00 | 64 | [84] Kamil Majchrzak v Sergiy Stakhovsky [146] | 6-3,6-3 | |
| Challenger Mouilleron le Captif | 10/08 15:15 | 25 | [115] Antoine Hoang v Sergiy Stakhovsky [146] | 6-3,3-6,6-4 | |
| Challenger Mouilleron le Captif | 10/07 17:55 | 24 | [146] Sergiy Stakhovsky v Constant Lestienne [215] | 7-5,7-5 | |
| Challenger Orleans | 09/27 13:00 | 27 | [263] Tristan Lamasine v Sergiy Stakhovsky [149] | 7-6,6-4 | |
| Challenger Orleans | 09/26 14:35 | 26 | [136] Yannick Maden v Sergiy Stakhovsky [149] | 7-6,3-6,4-6 | |
| Challenger Orleans | 09/25 12:00 | 25 | [149] Sergiy Stakhovsky v Ugo Humbert [65] | 4-6,7-5,7-6 | |
| Challenger Orleans | 09/23 17:55 | 24 | [149] Sergiy Stakhovsky v Antoine Cornut-Chauvinc [443] | 7-5,6-4 | |
| Davis Cup | 09/15 11:30 | - | [65] Marton Fucsovics v Sergiy Stakhovsky [147] | 7-5,3-6,6-7 | |
| Davis Cup | 09/14 09:00 | - | [136] Attila Balazs v Sergiy Stakhovsky [147] | 4-6,3-6 | |
| Challenger Cassis | 09/05 13:20 | 26 | [496] Rayane Roumane v Sergiy Stakhovsky [147] | 6-2,6-2 | |
| Challenger Cassis | 09/04 14:05 | 25 | [248] Tristan Lamasine v Sergiy Stakhovsky [147] | 6-2,6-7,1-6 | |
| Challenger Mallorca | 08/29 14:20 | 26 | [147] Sergiy Stakhovsky v Blaz Kavcic [239] | 4-6,2-6 | |
| Challenger Mallorca | 08/27 17:20 | 25 | [147] Sergiy Stakhovsky v Danilo Petrovic [247] | Retired | |
| US Open | 08/19 23:50 | 44 | [191] Nicola Kuhn v Sergiy Stakhovsky [146] | 6-4,6-4 | |
| Challenger Portoroz | 08/15 16:15 | 26 | [280] Zdenek Kolar v Sergiy Stakhovsky [147] | 6-2,3-6,6-3 | |
| Challenger Portoroz | 08/14 16:00 | 25 | [380] Alessandro Bega v Sergiy Stakhovsky [147] | 1-6,5-7 | |
| ATP Los Cabos | 07/28 01:20 | 64 | [250] Danilo Petrovic v Sergiy Stakhovsky [144] | 6-4,7-6 | |
| Challenger Binghamton | 07/24 19:00 | 25 | Alex Rybakov v Sergiy Stakhovsky | 7-6,4-6,7-6 | |
| ATP Newport | 07/16 16:50 | 25 | [134] Ramkumar Ramanathan v Sergiy Stakhovsky [145] | 5-7,7-6,6-2 | |
| Challenger Recanati | 07/04 17:00 | 26 | [196] Viktor Galovic v Sergiy Stakhovsky [136] | 5-7,6-3,6-3 | |
| Challenger Recanati | 07/03 19:05 | 25 | [385] Illya Marchenko v Sergiy Stakhovsky [136] | 6-7,6-3,5-7 | |
| Wimbledon | 06/26 12:25 | 45 | [220] Andrew Harris v Sergiy Stakhovsky [139] | 3-6,6-3,6-3 | |
| Wimbledon | 06/24 10:00 | 44 | [192] Darian King v Sergiy Stakhovsky [139] | 3-6,2-6 | |
| ATP Halle | 06/19 14:10 | 26 | [123] Sergiy Stakhovsky v Pierre-Hugues Herbert [43] | 6-2,6-7,4-6 | |
| ATP Halle | 06/18 11:30 | 25 | [152] Rudolf Molleker v Sergiy Stakhovsky [123] | 6-3,6-7,2-6 | |
| ATP Halle | 06/16 11:30 | 164 | [119] Matthias Bachinger v Sergiy Stakhovsky [121] | 4-6,7-6,2-6 | |
| ATP Halle | 06/15 10:25 | 64 | [121] Sergiy Stakhovsky v Ernests Gulbis [90] | 7-6,6-2 | |
| ATP Stuttgart | 06/09 09:00 | 164 | [194] Viktor Galovic v Sergiy Stakhovsky [111] | 6-4,2-6,6-4 | |
| ATP Stuttgart | 06/08 09:00 | 64 | [150] Adrian M-Maceiras v Sergiy Stakhovsky [111] | 3-6,4-6 | |
| Challenger Surbiton | 06/05 14:30 | 25 | [111] Sergiy Stakhovsky v James Ward [208] | 7-6,3-6,4-6 |