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