Stadium: Center Court Round: 26 Ground: Hardcourt outdoor
| Monterrey, Mexico | 2019/04/05 21:55 | Young, Donald v Klahn, Bradley | 7-5,6-4 |
| Winnetka, USA | 2019/07/10 17:10 | Klahn, Bradley v Max Purcell | 7-5,6-3 |
| Wimbledon, London, Great Britain | 2019/07/01 16:45 | Klahn, Bradley v David Goffin | 4-6,4-6,4-6 |
| Antalya, Turquie | 2019/06/25 10:30 | Jordan Thompson v Klahn, Bradley | 7-6,6-3 |
| Antalya, Turquie | 2019/06/24 10:30 | Klahn, Bradley v Darcis, Steve | 6-3,6-2 |
| London, Great Britain | 2019/06/15 10:00 | Tommy Paul v Klahn, Bradley | 6-1,6-4 |
| s-Hertogenbosch, Netherlands | 2019/06/08 16:35 | Klahn, Bradley v Arnaboldi, Andrea | 6-4,4-6,2-6 |
| French Open, Paris, France | 2019/05/27 09:00 | Alex De Minaur v Klahn, Bradley | 6-1,6-4,6-4 |
| Geneva, Switzerland | 2019/05/18 11:20 | Bernabe Zapata Miralles v Klahn, Bradley | 5-7,6-4,6-2 |
| Winnetka, USA | 2019/07/11 01:10 | Bangoura, Sekou v Young, Donald | 3-6,4-6 |
| Wimbledon, London, Great Britain | 2019/06/27 10:00 | Bemelmans, Ruben v Young, Donald | 6-4,6-4,6-1 |
| Wimbledon, London, Great Britain | 2019/06/26 10:00 | Young, Donald v Daniel Elahi Galan | 7-6,6-3 |
| Wimbledon, London, Great Britain | 2019/06/24 14:20 | Young, Donald v Egor Gerasimov | 6-4,7-6 |
| Challenger Columbus | 2019/06/12 20:00 | Young, Donald v Novikov, Dennis | 6-7,2-6 |
| Little Rock, USA | 2019/06/05 16:35 | Young, Donald v Zhizhen Zhang | 4-6,6-3,3-6 |
| French Open, Paris, France | 2019/05/20 08:00 | Marcos Giron v Young, Donald | 6-0,6-1 |
| Puerto Vallarta, Mexico | 2019/05/01 18:00 | Sarkissian, Alexander v Young, Donald | 1-6,7-6,6-2 |