| Challenger Cassis | 09/04 13:05 | 25 | [183] Oscar Otte v Sergiy Stakhovsky [138] | 7-6,3-6,7-5 | |
| Challenger Mallorca | 08/30 09:30 | 26 | [205] Kenny de Schepper v Sergiy Stakhovsky [138] | 6-2,6-4 | |
| Challenger Mallorca | 08/29 10:30 | 25 | [369] Emilio Gomez v Sergiy Stakhovsky [138] | 4-6,6-7 | |
| US Open | 08/22 16:30 | 44 | [379] Thai-Son Kwiatkowski v Sergiy Stakhovsky [138] | 6-4,3-6,6-1 | |
| Challenger Portoroz | 08/09 18:00 | 27 | [118] Sergiy Stakhovsky v Constant Lestienne [224] | 6-3,2-6,1-6 | |
| Challenger Portoroz | 08/08 17:20 | 26 | [118] Sergiy Stakhovsky v Altug Celikbilek [432] | 7-6,6-2 | |
| Challenger Portoroz | 08/07 20:05 | 25 | [118] Sergiy Stakhovsky v Christopher Heyman [304] | 4-6,6-3,6-3 | |
| Challenger Portoroz | 08/07 19:00 | 25 | Sergiy Stakhovsky v Blaz Rola | Cancelled | |
| Challenger Segovia | 07/31 14:10 | 25 | [117] Sergiy Stakhovsky v Matteo Viola [303] | 3-6,6-2,6-7 | |
| ATP Newport | 07/17 15:00 | 25 | [116] Sergiy Stakhovsky v Jason Jung [131] | 4-6,6-3,3-6 | |
| Wimbledon | 07/04 12:10 | 24 | [13] Sam Querrey v Sergiy Stakhovsky [109] | 7-6,6-3,6-3 | |
| Wimbledon | 07/02 10:30 | 23 | [109] Sergiy Stakhovsky v Joao Sousa [45] | 6-3,6-3,5-7,1-6,6-4 | |
| Boodles Challenge | 06/30 13:30 | 1 | [43] Andreas Seppi v Sergiy Stakhovsky [109] | 3-6,3-6 | |
| Boodles Challenge | 06/27 11:30 | 1 | [175] Liam Broady v Sergiy Stakhovsky [109] | 7-5,4-6,10-2 | |
| Challenger Ilkley | 06/24 14:00 | 29 | [140] Sergiy Stakhovsky v Oscar Otte [209] | 6-4,6-4 | |
| Challenger Ilkley | 06/23 13:00 | 28 | [140] Sergiy Stakhovsky v Michael Mmoh [133] | 6-4,7-5 | |
| Challenger Ilkley | 06/22 16:40 | 27 | [97] Jordan Thompson v Sergiy Stakhovsky [140] | 4-6,4-6 | |
| Challenger Ilkley | 06/20 17:20 | 26 | [165] Kevin King v Sergiy Stakhovsky [140] | 4-6,0-6 | |
| Challenger Ilkley | 06/18 15:35 | 25 | [168] Liam Broady v Sergiy Stakhovsky [140] | 6-1,6-7,2-6 | |
| Challenger Nottingham | 06/13 13:35 | 26 | Daniel Evans v Sergiy Stakhovsky | 7-5,7-6 | |
| Challenger Nottingham | 06/12 13:00 | 25 | [154] Mats Moraing v Sergiy Stakhovsky [133] | 3-6,5-7 | |
| Challenger Surbiton | 06/08 14:05 | 27 | [73] Matthew Ebden v Sergiy Stakhovsky [127] | 6-4,6-4 | |
| Challenger Surbiton | 06/07 10:00 | 26 | [127] Sergiy Stakhovsky v Ramkumar Ramanathan [121] | 6-4,7-6 | |
| Challenger Surbiton | 06/05 15:30 | 25 | [403] James Ward v Sergiy Stakhovsky [127] | 6-4,3-6,3-6 | |
| French Open | 05/31 11:00 | 24 | [127] Sergiy Stakhovsky v Mischa Zverev [64] | 3-6,7-6,6-7,1-6 | |
| French Open | 05/29 16:10 | 23 | [33] Feliciano Lopez v Sergiy Stakhovsky [127] | 2-6,4-6,2-6 | |
| French Open Qual | 05/24 13:55 | 46 | [119] Ilya Ivashka v Sergiy Stakhovsky [129] | 6-4,6-7,6-2 | |
| French Open Qual | 05/23 11:40 | 45 | [216] Constant Lestienne v Sergiy Stakhovsky [129] | 7-6,5-7,2-6 | |
| French Open Qual | 05/21 15:10 | 44 | [246] Egor Gerasimov v Sergiy Stakhovsky [129] | 3-6,6-1,6-7 | |
| Challenger Bordeaux | 05/15 12:50 | 25 | [130] Sergiy Stakhovsky v Zdenek Kolar [234] | 3-6,1-6 |