| Australian Open | 01/11 04:20 | 14 | [210] Jeffrey John Wolf v Sergiy Stakhovsky [220] | 6-3,6-4 | |
| Davis Cup | 11/27 14:35 | 1 | Casper Ruud v Sergiy Stakhovsky | 4-6,6-3,7-6 | |
| Challenger Pau | 11/20 13:00 | 28 | [137] Radu Albot v Sergiy Stakhovsky [233] | 6-2,6-7,6-1 | |
| Challenger Pau | 11/19 12:25 | 27 | [233] Sergiy Stakhovsky v Norbert Gombos [119] | 6-4,1-6,7-6 | |
| Challenger Pau | 11/18 12:05 | 26 | [233] Sergiy Stakhovsky v Dan Added [413] | 6-4,4-6,6-4 | |
| Challenger Pau | 11/16 17:15 | 25 | [118] Dennis Novak v Sergiy Stakhovsky [233] | 3-6,1-6 | |
| Challenger Bratislava | 11/09 09:30 | 25 | [229] Sergiy Stakhovsky v Jiri Lehecka [164] | 4-6,5-7 | |
| Challenger Bergamo | 11/03 18:15 | 26 | [415] Fabian Marozsan v Sergiy Stakhovsky [227] | 7-5,6-2 | |
| Challenger Bergamo | 11/01 15:00 | 25 | [227] Sergiy Stakhovsky v Matteo Arnaldi [363] | 6-3,6-7,7-6 | |
| Challenger Rennes | 09/14 08:00 | 25 | Sergiy Stakhovsky v Liam Broady | Cancelled | |
| Challenger Kyiv | 09/09 10:00 | 26 | [347] Ergi Kirkin v Sergiy Stakhovsky [227] | 4-6,6-3,6-2 | |
| Challenger Kyiv | 09/07 13:20 | 25 | [318] Jelle Sels v Sergiy Stakhovsky [227] | 2-6,3-6 | |
| US Open | 08/24 22:55 | 14 | [455] Zane Khan v Sergiy Stakhovsky [225] | 4-6,7-5,6-3 | |
| Challenger Nur-Sultan | 07/21 06:30 | 26 | [370] Nick Chappell v Sergiy Stakhovsky [229] | 7-6,6-4 | |
| Challenger Nur-Sultan | 07/20 07:20 | 25 | [474] Benjamin Lock v Sergiy Stakhovsky [229] | 3-6,6-3,5-7 | |
| Challenger Nur-Sultan | 07/15 06:00 | 26 | [226] Sergiy Stakhovsky v Jason Kubler [282] | 2-6,6-3,2-6 | |
| Challenger Nur-Sultan | 07/13 06:10 | 25 | [226] Sergiy Stakhovsky v Pavel Kotov [270] | 7-5,6-2 | |
| Challenger Porto | 07/03 10:00 | 28 | [247] Altug Celikbilek v Sergiy Stakhovsky [242] | 6-2,6-1 | |
| Challenger Porto | 07/02 12:00 | 27 | [297] Goncalo Oliveira v Sergiy Stakhovsky [242] | 6-7,6-7 | |
| Challenger Porto | 06/30 13:45 | 26 | [260] Matteo Viola v Sergiy Stakhovsky [242] | 2-6,6-4,5-7 | |
| Challenger Porto | 06/28 14:50 | 25 | [242] Sergiy Stakhovsky v Go Soeda [174] | 2-6,6-2,7-6 | |
| Wimbledon | 06/23 14:15 | 19 | [133] Gregoire Barrere v Sergiy Stakhovsky [239] | 7-5,6-3 | |
| Wimbledon | 06/22 14:50 | 14 | [218] Sergiy Stakhovsky v Go Soeda [163] | 6-3,7-6 | |
| ATP Halle | 06/12 15:10 | 14 | [210] Sergiy Stakhovsky v Arthur Rinderknech [118] | 4-6,4-6 | |
| ATP Stuttgart | 06/07 12:30 | 14 | [210] Sergiy Stakhovsky v Peter Gojowczyk [134] | 1-6,6-7 | |
| French Open | 05/26 11:55 | 15 | [112] Taro Daniel v Sergiy Stakhovsky [209] | 6-1,6-4 | |
| French Open | 05/25 08:30 | 14 | [226] Joao Domingues v Sergiy Stakhovsky [209] | 5-7,4-6 | |
| Challenger Prague | 05/06 10:00 | 26 | [213] Sergiy Stakhovsky v Sumit Nagal [140] | 6-4,1-6,4-6 | |
| Challenger Prague | 05/04 14:15 | 25 | [180] Dmitry Popko v Sergiy Stakhovsky [213] | 3-6,4-6 | |
| Challenger Prague | 05/03 11:30 | 19 | [204] Denis Istomin v Sergiy Stakhovsky [213] | 6-7,1-6 |