| Challenger Prague | 05/02 14:40 | 14 | Vojtech Petr v Sergiy Stakhovsky | 3-6,7-6,5-7 | |
| Challenger Ostrava | 04/28 09:00 | 26 | [193] Elias Ymer v Sergiy Stakhovsky [212] | 6-1,6-2 | |
| Challenger Ostrava | 04/27 09:10 | 25 | Patrik Rikl v Sergiy Stakhovsky | 4-6,2-6 | |
| Challenger Rome | 04/22 09:00 | 26 | [179] Lorenzo Giustino v Sergiy Stakhovsky [211] | 6-4,6-4 | |
| Challenger Rome | 04/20 11:40 | 25 | [211] Sergiy Stakhovsky v Mathias Bourgue [192] | 6-4,3-6,7-5 | |
| Challenger Lugano | 03/25 11:00 | 26 | [193] Sergiy Stakhovsky v Vitaliy Sachko [389] | 3-6,1-6 | |
| Challenger Lugano | 03/23 11:25 | 25 | [193] Sergiy Stakhovsky v Francesco Forti [442] | 6-4,6-2 | |
| Challenger Biella | 03/19 13:05 | 27 | [249] Daniel Masur v Sergiy Stakhovsky [195] | 7-6,6-4 | |
| Challenger Biella | 03/17 13:35 | 26 | [195] Sergiy Stakhovsky v Marc-Andrea Huesler [151] | 7-5,3-6,7-6 | |
| Challenger Biella | 03/15 15:45 | 25 | Sergiy Stakhovsky v Matteo Gigante | 7-5,5-7,6-2 | |
| Challenger Biella | 03/10 11:40 | 25 | [197] Sergiy Stakhovsky v Andreas Seppi [107] | 2-6,4-6 | |
| Davis Cup | 03/06 14:05 | - | [194] Sergiy Stakhovsky v Yshai Oliel [425] | 6-4,6-2 | |
| Davis Cup | 03/06 13:50 | 5 | Sergiy Stakhovsky v Daniel Cukierman | Cancelled | |
| Davis Cup | 03/05 15:35 | 2 | [194] Sergiy Stakhovsky v Edan Leshem [387] | 3-6,6-3,2-6 | |
| ATP Montpellier | 02/21 14:50 | 14 | [200] Sergiy Stakhovsky v Bernabe Zapata Miralles [142] | 1-6,0-6 | |
| Australian Open | 02/08 06:45 | 23 | [201] Sergiy Stakhovsky v Dusan Lajovic [26] | 7-5,4-6,3-6,7-5,4-6 | |
| ATP Great Ocean Road Open | 02/03 07:05 | 25 | [40] Reilly Opelka v Sergiy Stakhovsky [201] | 7-6,6-4 | |
| ATP Great Ocean Road Open | 02/02 07:40 | 24 | [182] Roman Safiullin v Sergiy Stakhovsky [201] | 7-6,4-6,3-6 | |
| Australian Open | 01/13 07:30 | 19 | Dane Sweeny v Sergiy Stakhovsky | 6-2,3-6,1-6 | |
| Australian Open | 01/12 09:20 | 15 | [259] Jason Kubler v Sergiy Stakhovsky [201] | 6-7,4-6 | |
| Australian Open | 01/10 14:45 | 60 | [201] Sergiy Stakhovsky v Bernabe Zapata Miralles [150] | 7-6,6-4 | |
| Challenger Bratislava | 11/13 10:00 | 27 | [195] Sergiy Stakhovsky v Maximilian Marterer [242] | Walkover | |
| Challenger Bratislava | 11/11 14:55 | 26 | [180] Roman Safiullin v Sergiy Stakhovsky [195] | 6-4,4-6,4-6 | |
| Challenger Bratislava | 11/10 16:35 | 25 | [192] Lukas Lacko v Sergiy Stakhovsky [195] | 5-7,6-7 | |
| Challenger Istanbul | 10/19 11:00 | 25 | [190] Sergiy Stakhovsky v Jay Clarke [187] | 4-6,0-6 | |
| French Open | 09/21 14:50 | 14 | [181] Sergiy Stakhovsky v Daniel Elahi Galan [151] | 6-7,3-6 | |
| Challenger Ostrava | 09/03 10:00 | 26 | [257] Mats Moraing v Sergiy Stakhovsky [173] | Retired | |
| Challenger Ostrava | 08/31 10:00 | 25 | [194] Peter Polansky v Sergiy Stakhovsky [173] | 6-4,4-6,3-6 | |
| Challenger Prague 2 | 08/26 10:25 | 26 | [173] Tallon Griekspoor v Sergiy Stakhovsky [168] | 6-1,6-1 | |
| Challenger Prague 2 | 08/24 13:20 | 25 | [195] Frederico Ferreira Silva v Sergiy Stakhovsky [168] | 6-2,6-7,6-7 |