Stadium: Court Central Round: 25 Ground: Hardcourt outdoor
| ATP Los Cabos | 2019/07/28 01:20 | Danilo Petrovic v Sergiy Stakhovsky | 6-4,7-6 |
| US Open | 2019/08/19 23:50 | Nicola Kuhn v Sergiy Stakhovsky | 6-4,6-4 |
| Challenger Portoroz | 2019/08/15 16:15 | Zdenek Kolar v Sergiy Stakhovsky | 6-2,3-6,6-3 |
| Challenger Portoroz | 2019/08/14 16:00 | Alessandro Bega v Sergiy Stakhovsky | 1-6,5-7 |
| ATP Los Cabos | 2019/07/28 01:20 | Danilo Petrovic v Sergiy Stakhovsky | 6-4,7-6 |
| Challenger Binghamton | 2019/07/24 19:00 | Alex Rybakov v Sergiy Stakhovsky | 7-6,4-6,7-6 |
| ATP Newport | 2019/07/16 16:50 | Ramkumar Ramanathan v Sergiy Stakhovsky | 5-7,7-6,6-2 |
| Challenger Recanati | 2019/07/04 17:00 | Viktor Galovic v Sergiy Stakhovsky | 5-7,6-3,6-3 |
| Challenger Recanati | 2019/07/03 19:05 | Illya Marchenko v Sergiy Stakhovsky | 6-7,6-3,5-7 |
| Challenger Mallorca | 2019/08/26 09:00 | Aaron Cohen v Danilo Petrovic | 3-6,2-6 |
| Challenger Portoroz | 2019/08/13 09:10 | Danilo Petrovic v Lukas Klein | 3-6,4-6 |
| ATP Los Cabos | 2019/07/29 01:40 | Jason Jung v Danilo Petrovic | 6-4,7-6 |
| ATP Los Cabos | 2019/07/28 01:20 | Danilo Petrovic v Sergiy Stakhovsky | 6-4,7-6 |
| Challenger Granby | 2019/07/25 18:25 | Danilo Petrovic v Yasutaka Uchiyama | 4-6,4-6 |
| Challenger Granby | 2019/07/23 14:00 | Danilo Petrovic v Alexander Sarkissian | 7-6,6-4 |
| Challenger Gatineau | 2019/07/15 19:20 | Michael Redlicki v Danilo Petrovic | 6-3,4-6,7-5 |
| Challenger Milan | 2019/06/30 15:30 | Hugo Dellien v Danilo Petrovic | 7-5,6-4 |