Stadium: Lotto RLP Centre Court Ground: Hardcourt indoor
| Challenger Da Nang | 2019/01/06 06:50 | Benjamin Hassan v Jeremy Jahn | 6-2,1-6,6-3 |
| Challenger Heilbronn Qual | 2018/05/14 10:00 | Benjamin Hassan v Jeremy Jahn | 6-2,2-6,6-4 |
| Challenger Campinas | 2019/10/01 16:20 | Nicolas Alvarez v Jeremy Jahn | 6-4,6-2 |
| Challenger Biella | 2019/09/18 11:15 | Alejandro Davidovich Fokina v Jeremy Jahn | 7-5,7-5 |
| Challenger Biella | 2019/09/16 14:10 | Jeremy Jahn v Enrico Dalla Valle | 6-3,6-4 |
| Challenger Szczecin | 2019/09/13 12:00 | Albert Ramos-Vinolas v Jeremy Jahn | 7-6,6-2 |
| Challenger Szczecin | 2019/09/12 12:45 | Jeremy Jahn v Gianluca Mager | 6-1,2-6,6-4 |
| Challenger Szczecin | 2019/09/11 08:00 | Rudolf Molleker v Jeremy Jahn | 4-6,3-6 |
| Challenger Szczecin | 2019/09/10 14:00 | Vit Kopriva v Jeremy Jahn | 5-7,4-6 |
| ITF M25 La Marsa | 2019/09/06 10:00 | Bruno Santanna v Jeremy Jahn | 6-1,6-2 |
| Challenger Ortisei | 2019/11/11 14:00 | Lorenzo Musetti v Benjamin Hassan | 6-4,6-2 |
| Challenger Ismaning | 2019/10/16 08:00 | Adrian Menendez-Maceiras v Benjamin Hassan | 6-2,6-4 |
| Challenger Glasgow | 2019/09/16 19:25 | Benjamin Hassan v Luca Vanni | 4-6,1-6 |
| Davis Cup | 2019/09/14 10:15 | Benjamin Hassan v Sanjar Fayziev | 2-6,6-3,6-4 |
| Davis Cup | 2019/09/13 11:15 | Benjamin Hassan v Khumoyun Sultanov | 2-6,6-3,7-5 |
| Challenger Meerbusch | 2019/08/15 11:00 | Carlos Taberner v Benjamin Hassan | 7-6,6-3 |
| Challenger Augsburg | 2019/08/08 09:00 | Benjamin Hassan v Facundo Mena | 6-4,1-6,0-6 |
| Challenger Augsburg | 2019/08/06 14:30 | Lukas Rosol v Benjamin Hassan | 4-6,4-6 |