| ATP Shanghai Qual | 10/07 05:20 | 45 | [54] Leonardo Mayer v Sergiy Stakhovsky [103] | 7-6,3-6,7-6 | |
| ATP Beijing Qual | 10/01 06:20 | 46 | [80] Malek Jaziri v Sergiy Stakhovsky [98] | 6-4,7-6 | |
| ATP Beijing Qual | 09/30 05:25 | 45 | [126] Thiago Monteiro v Sergiy Stakhovsky [98] | 7-6,5-7,3-6 | |
| ATP Shenzhen | 09/28 06:00 | 26 | Sergiy Stakhovsky v Alexandr Dolgopolov | 6-7,4-6 | |
| ATP Shenzhen | 09/26 08:40 | 25 | [93] Nicolas Kicker v Sergiy Stakhovsky [98] | 3-6,3-6 | |
| Challenger Izmir | 09/21 09:00 | 26 | [99] Sergiy Stakhovsky v Illya Marchenko [287] | 6-7,3-6 | |
| Challenger Izmir | 09/20 08:00 | 25 | [99] Sergiy Stakhovsky v Dmitry Popko [196] | 6-2,7-6 | |
| US Open Qual | 08/25 16:10 | 46 | [97] Sergiy Stakhovsky v Vaclav Safranek [206] | 6-3,5-7,1-6 | |
| US Open Qual | 08/24 16:50 | 45 | [97] Sergiy Stakhovsky v Felix Auger Aliassime [227] | 7-6,6-4 | |
| US Open Qual | 08/22 15:00 | 44 | [97] Sergiy Stakhovsky v Alexey Vatutin [183] | 6-2,6-1 | |
| Challenger Portoroz | 08/12 18:00 | 29 | [162] Matteo Berrettini v Sergiy Stakhovsky [115] | 7-6,6-7,3-6 | |
| Challenger Portoroz | 08/11 17:10 | 28 | [115] Sergiy Stakhovsky v Stefanos Tsitsipas [168] | 4-6,6-4,7-5 | |
| Challenger Portoroz | 08/10 20:15 | 27 | [109] Filip Krajinovic v Sergiy Stakhovsky [115] | 1-6,6-3,3-6 | |
| Challenger Portoroz | 08/09 14:20 | 26 | [305] Albano Olivetti v Sergiy Stakhovsky [115] | 2-6,2-6 | |
| Challenger Portoroz | 08/08 14:20 | 25 | [287] Matteo Viola v Sergiy Stakhovsky [115] | 6-7,2-6 | |
| Challenger Segovia | 08/01 13:10 | 25 | [275] Steven Diez v Sergiy Stakhovsky [113] | 2-6,7-6,6-3 | |
| ATP Hamburg Qual | 07/23 11:00 | 46 | [79] Damir Dzumhur v Sergiy Stakhovsky [114] | 7-6,7-5 | |
| ATP Hamburg Qual | 07/22 12:35 | 45 | Jason J Hildebrandt v Sergiy Stakhovsky | 2-6,4-6 | |
| Challenger Scheveningen | 07/19 14:20 | 26 | [230] Simone Bolelli v Sergiy Stakhovsky [114] | 6-4,3-6,6-3 | |
| Challenger Scheveningen | 07/17 12:00 | 25 | George Von Massow v Sergiy Stakhovsky | 6-7,2-6 | |
| Wimbledon | 07/05 12:00 | 24 | [9] Kei Nishikori v Sergiy Stakhovsky [122] | 6-4,6-7,6-1,7-6 | |
| Wimbledon | 07/03 13:20 | 23 | [81] Julien Benneteau v Sergiy Stakhovsky [122] | 3-6,6-7,6-2,2-6 | |
| Wimbledon Qual | 06/29 10:00 | 46 | [122] Sergiy Stakhovsky v Tatsuma Ito [181] | Cancelled | |
| Wimbledon Qual | 06/28 15:05 | 45 | [122] Sergiy Stakhovsky v Roberto Quiroz [238] | 6-3,7-5 | |
| Wimbledon Qual | 06/26 11:45 | 44 | [122] Sergiy Stakhovsky v Kenny de Schepper [151] | 6-3,6-4 | |
| Challenger Nottingham | 06/16 10:00 | 27 | [103] Thomas Fabbiano v Sergiy Stakhovsky [106] | 4-6,6-2,7-6 | |
| Challenger Nottingham | 06/14 11:50 | 26 | [106] Sergiy Stakhovsky v Illya Marchenko [121] | 6-4,7-6 | |
| Challenger Nottingham | 06/13 13:05 | 25 | [106] Sergiy Stakhovsky v Akira Santillan [194] | 6-4,7-6 | |
| Challenger Surbiton | 06/10 09:30 | 27 | [94] Marius Copil v Sergiy Stakhovsky [123] | 7-5,6-4 | |
| Challenger Surbiton | 06/08 15:40 | 26 | [123] Sergiy Stakhovsky v Cameron Norrie [243] | 6-4,7-6 |