Stadium: Center Court Round: 24 Ground: Carpet indoor
| ATP Geneva | 2019/05/18 09:35 | Lorenzo Sonego v Daniel Masur | 4-6,6-2,6-3 |
| Challenger Heilbronn | 2019/05/15 12:05 | Daniel Masur v Jiri Vesely | 5-7,4-6 |
| Challenger Heilbronn | 2019/05/14 10:50 | Daniel Masur v Yannick Hanfmann | 6-3,4-6,6-2 |
| Challenger Heilbronn | 2019/05/13 09:30 | Kevin Krawietz v Daniel Masur | 4-6,3-6 |
| Challenger Aix en Provence | 2019/05/10 16:15 | Daniel Masur v Hugo Nys | 6-4,5-7,5-7 |
| Challenger Aix en Provence | 2019/05/09 15:00 | Lloyd Harris v Daniel Masur | 4-6,3-6 |
| Challenger Aix en Provence | 2019/05/08 12:00 | Daniel Masur v Jonathan Kanar | 6-2,6-3 |
| Challenger Aix en Provence | 2019/05/06 13:00 | Kenny de Schepper v Daniel Masur | 5-7,6-4,1-6 |
| French Open | 2019/05/21 08:00 | Lucas Miedler v Evgeny Karlovskiy | 7-5,6-2 |
| Challenger Lisbon | 2019/05/14 14:30 | Evgeny Karlovskiy v Roberto Carballes Baena | 6-3,5-7,4-6 |
| Challenger Lisbon | 2019/05/13 10:55 | Riccardo Bonadio v Evgeny Karlovskiy | 0-6,3-6 |
| Challenger Braga | 2019/05/08 15:30 | Bernabe Zapata Miralles v Evgeny Karlovskiy | 6-1,6-4 |
| Challenger Tallahassee | 2019/04/25 16:00 | Noah Rubin v Evgeny Karlovskiy | 3-6,6-4,7-5 |
| Challenger Tallahassee | 2019/04/24 17:15 | Tomas Barrios Vera v Evgeny Karlovskiy | 3-6,6-1,3-6 |
| Challenger Sarasota | 2019/04/15 19:45 | Evgeny Karlovskiy v Collin Altamirano | 7-6,4-6,4-6 |
| ATP Marrakech | 2019/04/08 10:00 | Alejandro Davidovich Fokina v Evgeny Karlovskiy | 6-2,6-2 |