Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2019/07/08 17:50 | Brydan Klein v Bernardo Saraiva | 6-1,6-2 |
| Challenger Ilkley | 2019/06/19 15:05 | Brydan Klein v Mikael Ymer | 3-6,1-6 |
| Challenger Ilkley | 2019/06/18 13:20 | Jan Choinski v Brydan Klein | 6-2,5-7,2-6 |
| Challenger Ilkley | 2019/06/17 11:00 | Evgeny Karlovskiy v Brydan Klein | 6-4,1-6,2-6 |
| Challenger Nottingham | 2019/06/11 14:40 | Ryan Peniston v Brydan Klein | 4-6,6-4,6-4 |
| Challenger Nottingham | 2019/06/10 13:35 | Brydan Klein v Lloyd Glasspool | 7-6,6-2 |
| Challenger Surbiton | 2019/06/05 11:50 | Brydan Klein v Brayden Schnur | 3-6,3-6 |
| Challenger Surbiton | 2019/06/03 14:10 | Andrew Harris v Brydan Klein | 6-2,3-6,4-6 |
| Wimbledon | 2019/06/24 10:00 | Darian King v Sergiy Stakhovsky | 3-6,2-6 |
| 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 |