Stadium: Court 3 Round: 25 Ground: Grass
| Challenger Surbiton | 2018/06/05 15:30 | James Ward v Sergiy Stakhovsky | 6-4,3-6,3-6 |
| French Open | 2019/05/27 13:15 | Sergiy Stakhovsky v Gilles Simon | 3-6,3-6,4-6 |
| French Open | 2019/05/23 13:05 | Sergiy Stakhovsky v Alexey Vatutin | 4-6,6-1,3-6 |
| French Open | 2019/05/22 10:25 | Sergiy Stakhovsky v Uladzimir Ignatik | 7-6,6-4 |
| Challenger Gwangju | 2019/05/16 05:05 | Tung-Lin Wu v Sergiy Stakhovsky | 6-4,6-3 |
| Challenger Gwangju | 2019/05/14 03:45 | Tsung-Hua Yang v Sergiy Stakhovsky | 4-6,6-7 |
| Challenger Busan | 2019/05/08 03:00 | Kaichi Uchida v Sergiy Stakhovsky | 7-6,6-3 |
| Challenger Seoul | 2019/05/02 04:55 | Nikola Milojevic v Sergiy Stakhovsky | 6-2,7-6 |
| Challenger Seoul | 2019/04/30 05:30 | Rio Noguchi v Sergiy Stakhovsky | 1-6,4-6 |
| Challenger Surbiton | 2019/06/03 13:30 | Paul Jubb v James Ward | 5-7,6-4,3-6 |
| French Open | 2019/05/20 15:00 | James Ward v Oscar Otte | 1-6,2-6 |
| Challenger Aix en Provence | 2019/05/07 13:20 | James Ward v Gianluca Mager | 6-7,2-6 |
| Challenger Aix en Provence | 2019/05/06 13:00 | James Ward v Tristan Lamasine | 7-6,7-6 |
| Challenger Puerto Vallarta | 2019/05/02 21:35 | Yusuke Takahashi v James Ward | 2-6,6-4,6-3 |
| Challenger Puerto Vallarta | 2019/05/01 20:35 | Facundo Mena v James Ward | 4-6,3-6 |
| Challenger Leon | 2019/04/27 20:00 | Blaz Rola v James Ward | 6-7,6-3,7-6 |
| Challenger Leon | 2019/04/26 21:25 | James Ward v Marcelo Arevalo | 6-3,6-4 |