Stadium: Centre Court Round: 29 Ground: Clay
| US Open MD | 2019/08/29 22:45 | Jebavy/Middelkoop v Haase/Koolhof | 4-6,4-6 |
| Challenger Meerbusch MD | 2019/08/16 11:00 | Jebavy/Middelkoop v Balaji/Vardhan | 6-7,3-6 |
| Challenger Meerbusch MD | 2019/08/13 13:30 | Jebavy/Middelkoop v Mena/Merino | 7-5,6-3 |
| ATP Kitzbuhel MD | 2019/08/02 09:30 | Jebavy/Middelkoop v Oswald/Polasek | 2-6,6-3,3-10 |
| ATP Kitzbuhel MD | 2019/07/31 10:00 | Fabbiano/Podlipnik-Castillo v Jebavy/Middelkoop | 4-6,1-6 |
| ATP Kitzbuhel MD | 2019/07/29 12:30 | Molchanov/Zelenay v Jebavy/Middelkoop | 4-6,3-6 |
| ATP Hamburg MD | 2019/07/24 14:30 | Jebavy/Middelkoop v Krawietz/Mies | 5-7,7-6,10-12 |
| ATP Bastad MD | 2019/07/19 12:00 | Jebavy/Middelkoop v Gille/Vliegen | 6-4,4-6,5-10 |