Stadium: Center Round: 25 Ground: Clay
| Wimbledon | 2019/06/26 10:00 | Dustin Brown v Mikael Ymer | 6-7,2-6 |
| Wimbledon | 2019/06/24 15:45 | Zhe Li v Dustin Brown | 6-7,3-6 |
| ATP Stuttgart | 2019/06/14 13:00 | Dustin Brown v Felix Auger Aliassime | 6-7,7-6,6-7 |
| ATP Stuttgart | 2019/06/13 13:05 | Alexander Zverev v Dustin Brown | 4-6,7-6,3-6 |
| ATP Stuttgart | 2019/06/11 10:50 | Dustin Brown v John Millman | 6-4,7-6 |
| ATP Stuttgart | 2019/06/09 09:00 | Dustin Brown v Gregoire Barrere | 6-2,7-6 |
| ATP Stuttgart | 2019/06/08 12:50 | Denis Istomin v Dustin Brown | 5-7,4-6 |
| Challenger Surbiton | 2019/06/03 10:00 | Dustin Brown v Lukas Lacko | 3-6,2-6 |
| Challenger Ludwigshafen | 2019/07/01 11:50 | Alexey Vatutin v Sebastian Fanselow | 7-5,2-6,6-7 |
| Challenger Milan | 2019/06/27 14:00 | Aslan Karatsev v Sebastian Fanselow | 6-4,6-2 |
| Challenger Milan | 2019/06/26 13:30 | Sebastian Fanselow v Paolo Lorenzi | 6-4,7-5 |
| Challenger Milan | 2019/06/24 15:30 | Sebastian Fanselow v Christopher Heyman | 7-5,7-6 |
| Challenger Bratislava | 2019/06/19 08:00 | Sebastian Fanselow v Alexey Vatutin | 4-6,4-6 |
| Challenger Bratislava | 2019/06/17 09:20 | Sebastian Fanselow v Alex Molcan | 7-6,6-3 |
| Challenger Morelos | 2019/02/19 18:00 | Matias Franco Descotte v Sebastian Fanselow | 6-4,6-2 |
| Challenger Chennai | 2019/02/05 06:05 | Mukund Sasikumar v Sebastian Fanselow | 6-3,6-1 |