Stadium: Court 14 Round: 44 Ground: Grass
| Challenger Little Rock | 2019/06/08 21:00 | Duckhee Lee v Darian King | 6-0,6-0 |
| Challenger Little Rock | 2019/06/08 16:10 | Darian King v Raymond Sarmiento | 6-3,6-7,7-5 |
| Challenger Little Rock | 2019/06/07 23:10 | Darian King v Zhe Li | 7-6,6-3 |
| Challenger Little Rock | 2019/06/05 18:40 | Darian King v Oliver Crawford | 6-4,6-4 |
| French Open | 2019/05/20 08:00 | Peter Polansky v Darian King | 6-4,6-4 |
| Challenger Puerto Vallarta | 2019/05/04 00:00 | Darian King v Alejandro Tabilo | 1-6,7-5,5-7 |
| Challenger Puerto Vallarta | 2019/05/03 02:45 | Joao Menezes v Darian King | 5-7,5-7 |
| Challenger Puerto Vallarta | 2019/05/01 17:00 | Andres Artunedo Martinavarr v Darian King | 4-6,4-6 |
| 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 |
| ATP Halle | 2019/06/16 11:30 | Matthias Bachinger v Sergiy Stakhovsky | 4-6,7-6,2-6 |
| ATP Halle | 2019/06/15 10:25 | Sergiy Stakhovsky v Ernests Gulbis | 7-6,6-2 |
| ATP Stuttgart | 2019/06/09 09:00 | Viktor Galovic v Sergiy Stakhovsky | 6-4,2-6,6-4 |
| ATP Stuttgart | 2019/06/08 09:00 | Adrian Menendez-Maceiras v Sergiy Stakhovsky | 3-6,4-6 |
| Challenger Surbiton | 2019/06/05 14:30 | Sergiy Stakhovsky v James Ward | 7-6,3-6,4-6 |
| French Open | 2019/05/27 13:15 | Sergiy Stakhovsky v Gilles Simon | 3-6,3-6,4-6 |