Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2019/07/08 17:50 | Klein, Brydan v Saraiva, Bernardo | 6-1,6-2 |
| Ilkley, Great Britain | 2019/06/19 15:05 | Klein, Brydan v Ymer, Mikael | 3-6,1-6 |
| Ilkley, Great Britain | 2019/06/18 13:20 | Jan Choinski v Klein, Brydan | 6-2,5-7,2-6 |
| Ilkley, Great Britain | 2019/06/17 11:00 | Evgeny Karlovskiy v Klein, Brydan | 6-4,1-6,2-6 |
| Challenger - Nottingham | 2019/06/11 14:40 | Ryan Peniston v Klein, Brydan | 4-6,6-4,6-4 |
| Challenger - Nottingham | 2019/06/10 13:35 | Klein, Brydan v Glasspool, Lloyd | 7-6,6-2 |
| Surbiton, Great Britain | 2019/06/05 11:50 | Klein, Brydan v Schnur, Brayden | 3-6,3-6 |
| Surbiton, Great Britain | 2019/06/03 14:10 | Harris, Andrew v Klein, Brydan | 6-2,3-6,4-6 |
| Wimbledon, London, Great Britain | 2019/06/24 10:00 | Darian King v Stakhovsky, Sergiy | 3-6,2-6 |
| Little Rock, USA | 2019/06/08 21:00 | Duckhee Lee v Darian King | 6-0,6-0 |
| Little Rock, USA | 2019/06/08 16:10 | Darian King v Sarmiento, Raymond | 6-3,6-7,7-5 |
| Little Rock, USA | 2019/06/07 23:10 | Darian King v Li, Zhe | 7-6,6-3 |
| Little Rock, USA | 2019/06/05 18:40 | Darian King v Oliver Crawford | 6-4,6-4 |
| French Open, Paris, France | 2019/05/20 08:00 | Polansky, Peter v Darian King | 6-4,6-4 |
| Puerto Vallarta, Mexico | 2019/05/04 00:00 | Darian King v Alejandro Tabilo | 1-6,7-5,5-7 |
| Puerto Vallarta, Mexico | 2019/05/03 02:45 | Joao Menezes v Darian King | 5-7,5-7 |