| Challenger Aix en Provence | 05/08 08:30 | 25 | [148] Sebastian Ofner v Sergiy Stakhovsky [127] | 3-6,6-2,7-5 | |
| Challenger Ostrava | 05/01 14:00 | 25 | [289] Arthur De Greef v Sergiy Stakhovsky [126] | 6-4,3-6,6-3 | |
| ATP Budapest Qual | 04/21 10:25 | 26 | [133] Elias Ymer v Sergiy Stakhovsky [121] | 6-3,6-3 | |
| ATP Monte Carlo Qual | 04/15 11:45 | 46 | [117] Sergiy Stakhovsky v Dusan Lajovic [90] | 4-6,4-6 | |
| ATP Monte Carlo Qual | 04/14 12:35 | 45 | [68] Viktor Troicki v Sergiy Stakhovsky [117] | 1-6,3-6 | |
| Challenger St Brieuc | 03/28 14:00 | 25 | [118] Sergiy Stakhovsky v Tobias Kamke [214] | 4-6,3-6 | |
| ATP Miami Qual | 03/20 20:55 | 45 | [103] Ricardas Berankis v Sergiy Stakhovsky [118] | 3-6,6-3,6-0 | |
| ATP Miami Qual | 03/19 18:55 | 44 | [188] Evan King v Sergiy Stakhovsky [118] | 3-6,6-4,6-7 | |
| Challenger Irving | 03/14 21:20 | 25 | Sergiy Stakhovsky v Steve Johnson | 7-5,6-7,4-6 | |
| ATP Indian Wells Qual | 03/07 21:30 | 45 | Cameron Norrie v Sergiy Stakhovsky | 6-4,6-2 | |
| ATP Indian Wells Qual | 03/07 02:00 | 44 | Marcos Giron v Sergiy Stakhovsky | 7-5,6-7,4-6 | |
| Challenger Indian Wells | 02/26 21:20 | 25 | Sergiy Stakhovsky v Martin Klizan | 3-6,6-2,3-6 | |
| ATP Marseille | 02/21 13:00 | 25 | Gilles Muller v Sergiy Stakhovsky | 7-5,6-3 | |
| ATP Marseille Qual | 02/19 13:10 | - | Sergiy Stakhovsky v Norbert Gombos | 4-6,2-6 | |
| ATP Marseille Qual | 02/18 11:40 | 26 | Sergiy Stakhovsky v Matthias Bachinger | 1-6,6-1,7-5 | |
| ATP Sofia | 02/06 10:00 | 25 | Sergiy Stakhovsky v Mirza Basic | Cancelled | |
| Davis Cup | 02/03 13:35 | 26 | Sergiy Stakhovsky v Elias Ymer | 6-4,6-4 | |
| Davis Cup | 02/02 15:00 | 26 | Sergiy Stakhovsky v Mikael Ymer | 6-7,2-6 | |
| Challenger Rennes | 01/24 16:05 | 25 | Elias Ymer v Sergiy Stakhovsky | 6-1,3-6,6-3 | |
| Challenger Koblenz | 01/20 15:10 | 28 | Sergiy Stakhovsky v Mats Moraing | 4-6,3-6 | |
| Challenger Koblenz | 01/19 18:25 | 27 | Mohamed Safwat v Sergiy Stakhovsky | 2-6,1-6 | |
| Challenger Koblenz | 01/18 17:00 | 26 | Nicola Kuhn v Sergiy Stakhovsky | 4-6,3-6 | |
| Challenger Koblenz | 01/17 13:00 | 25 | Joris De Loore v Sergiy Stakhovsky | 2-6,3-6 | |
| Australian Open Qual | 01/10 02:40 | 44 | Sergiy Stakhovsky v Matthias Bachinger | 6-4,6-7,3-6 | |
| Challenger Playford | 01/02 02:45 | 25 | Tommy Paul v Sergiy Stakhovsky | 3-6,7-5,7-5 | |
| Challenger Bratislava | 11/07 19:30 | 25 | [163] Andrej Martin v Sergiy Stakhovsky [110] | 7-6,6-3 | |
| ATP Vienna Qual | 10/22 11:00 | 46 | [102] Sergiy Stakhovsky v Guillermo Garcia-Lopez [82] | 6-3,3-6,1-6 | |
| ATP Vienna Qual | 10/21 11:15 | 45 | [55] Nikoloz Basilashvili v Sergiy Stakhovsky [102] | 1-6,5-7 | |
| ATP Antwerp | 10/18 10:00 | 26 | [61] Joao Sousa v Sergiy Stakhovsky [102] | 5-7,6-4,6-4 | |
| ATP Antwerp | 10/16 13:30 | 25 | [102] Sergiy Stakhovsky v Jared Donaldson [52] | 7-6,6-4 |