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