Stadium: Court 1 Round: 64 Ground: Hardcourt outdoor
| 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 |
| Challenger Milan | 2019/06/29 14:00 | Danilo Petrovic v Sumit Nagal | 7-5,6-2 |
| Challenger Milan | 2019/06/28 14:00 | Danilo Petrovic v Frederico Ferreira Silva | 6-3,6-4 |
| Challenger Milan | 2019/06/27 08:00 | Danilo Petrovic v Nino Serdarusic | 6-3,7-5 |
| Challenger Milan | 2019/06/26 09:30 | Duckhee Lee v Danilo Petrovic | 2-6,2-6 |
| 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 |
| Wimbledon | 2019/06/26 12:25 | Andrew Harris v Sergiy Stakhovsky | 3-6,6-3,6-3 |
| Wimbledon | 2019/06/24 10:00 | Darian King v Sergiy Stakhovsky | 3-6,2-6 |
| ATP Halle | 2019/06/19 14:10 | Sergiy Stakhovsky v Pierre-Hugues Herbert | 6-2,6-7,4-6 |
| ATP Halle | 2019/06/18 11:30 | Rudolf Molleker v Sergiy Stakhovsky | 6-3,6-7,2-6 |