| French Open | 05/27 13:15 | 23 | [111] Sergiy Stakhovsky v Gilles Simon [33] | 3-6,3-6,4-6 | |
| French Open | 05/23 13:05 | 46 | [111] Sergiy Stakhovsky v Alexey Vatutin [216] | 4-6,6-1,3-6 | |
| French Open | 05/22 10:25 | 45 | [111] Sergiy Stakhovsky v Uladzimir Ignatik [263] | 7-6,6-4 | |
| French Open | 05/20 11:35 | 44 | [111] Sergiy Stakhovsky v James Duckworth [151] | Retired | |
| Challenger Gwangju | 05/16 05:05 | 26 | [287] Tung-Lin Wu v Sergiy Stakhovsky [112] | 6-4,6-3 | |
| Challenger Gwangju | 05/14 03:45 | 25 | [290] Tsung-Hua Yang v Sergiy Stakhovsky [112] | 4-6,6-7 | |
| Challenger Busan | 05/08 03:00 | 25 | [245] Kaichi Uchida v Sergiy Stakhovsky [114] | 7-6,6-3 | |
| Challenger Seoul | 05/02 04:55 | 26 | [148] Nikola Milojevic v Sergiy Stakhovsky [115] | 6-2,7-6 | |
| Challenger Seoul | 04/30 05:30 | 25 | Rio Noguchi v Sergiy Stakhovsky | 1-6,4-6 | |
| ATP Budapest | 04/22 15:50 | 25 | [44] Radu Albot v Sergiy Stakhovsky [115] | 7-5,6-4 | |
| ATP Budapest | 04/21 09:00 | 164 | [91] Miomir Kecmanovic v Sergiy Stakhovsky [115] | 6-4,6-4 | |
| ATP Budapest | 04/20 08:30 | 64 | [170] Daniel Brands v Sergiy Stakhovsky [115] | 5-7,1-6 | |
| Challenger Taipei | 04/14 07:30 | 29 | [156] Dennis Novak v Sergiy Stakhovsky [124] | 6-2,6-4 | |
| Challenger Taipei | 04/13 06:30 | 28 | [124] Sergiy Stakhovsky v Go Soeda [207] | 7-6,7-6 | |
| Challenger Taipei | 04/12 07:20 | 27 | [148] Tatsuma Ito v Sergiy Stakhovsky [124] | 6-7,7-6,4-6 | |
| Challenger Taipei | 04/11 05:00 | 26 | [202] Maxime Janvier v Sergiy Stakhovsky [124] | 5-7,4-6 | |
| Challenger Taipei | 04/10 06:45 | 25 | [284] Stephane Robert v Sergiy Stakhovsky [124] | 6-7,2-6 | |
| Challenger St Brieuc | 03/26 20:05 | 25 | [210] Maxime Janvier v Sergiy Stakhovsky [127] | 6-3,7-6 | |
| Challenger St Brieuc | 03/25 09:00 | 166 | [127] Sergiy Stakhovsky v Yannick Mertens [441] | 6-3,6-4 | |
| Challenger Lille | 03/20 17:30 | 25 | [437] Aslan Karatsev v Sergiy Stakhovsky [127] | 6-3,6-4 | |
| Challenger Pau | 02/26 19:30 | 25 | [264] Norbert Gombos v Sergiy Stakhovsky [126] | 7-6,4-6,6-1 | |
| ATP Marseille | 02/22 18:00 | 27 | [12] Stefanos Tsitsipas v Sergiy Stakhovsky [141] | 6-4,6-3 | |
| ATP Marseille | 02/21 19:25 | 26 | [141] Sergiy Stakhovsky v Gregoire Barrere [130] | 6-3,6-4 | |
| ATP Marseille | 02/19 11:00 | 25 | [168] Constant Lestienne v Sergiy Stakhovsky [141] | 6-7,6-1,3-6 | |
| ATP Marseille | 02/18 12:45 | 164 | [141] Sergiy Stakhovsky v Constant Lestienne [168] | 5-7,6-1,5-7 | |
| ATP Marseille | 02/17 13:55 | 64 | [136] Sergiy Stakhovsky v Mirza Basic [168] | 4-6,6-1,6-3 | |
| ATP Rotterdam | 02/09 15:50 | 64 | [136] Sergiy Stakhovsky v Ernests Gulbis [83] | 3-6,4-6 | |
| ATP Sofia | 02/04 12:30 | 164 | [136] Sergiy Stakhovsky v Daniel Brands [180] | 4-6,6-7 | |
| ATP Sofia | 02/03 14:05 | 64 | Sergiy Stakhovsky v Gabriel Donev | 6-1,6-2 | |
| Challenger Quimper | 01/31 11:45 | 26 | [136] Sergiy Stakhovsky v Tobias Kamke [218] | 6-3,3-6,6-7 |