Stadium: CT Dolomia Serena Round: 29 Ground: Clay
| Challenger Augsburg | 2019/08/06 12:50 | Jeremy Jahn v Pedro Martinez | 5-7,6-4,6-7 |
| Challenger Augsburg | 2019/08/05 14:05 | Javier Barranco Cosano v Jeremy Jahn | 2-6,3-6 |
| Challenger Sopot | 2019/08/01 14:10 | Jan Choinski v Jeremy Jahn | 6-3,6-7,6-4 |
| Challenger Sopot | 2019/07/31 12:00 | Jeremy Jahn v Kamil Majchrzak | 6-7,6-1,7-5 |
| Challenger Sopot | 2019/07/29 15:00 | Pedro Sakamoto v Jeremy Jahn | 3-6,3-6 |
| ITF M25 Lasne | 2019/07/07 12:30 | Jeroen Vanneste v Jeremy Jahn | 6-1,7-5 |
| ITF M25 Lasne | 2019/07/06 12:00 | Jeremy Jahn v Markus Eriksson | 7-5,7-6 |
| ITF M25 Lasne | 2019/07/05 13:00 | Zizou Bergs v Jeremy Jahn | 6-4,2-6,6-7 |
| Challenger Sopot | 2019/08/01 10:30 | Aslan Karatsev v Christopher O'Connell | 6-2,6-1 |
| Challenger Sopot | 2019/07/31 09:35 | Christopher O'Connell v Tommy Robredo | 6-4,7-6 |
| Challenger Sopot | 2019/07/30 08:00 | Christopher O'Connell v Enrico Dalla Valle | 6-0,6-2 |
| Challenger Tampere | 2019/07/24 11:15 | Christopher O'Connell v Pedja Krstin | 4-6,6-1,3-6 |
| Challenger Tampere | 2019/07/23 08:55 | Christopher O'Connell v Khumoyun Sultanov | 7-5,6-4 |
| Challenger San Benedetto | 2019/07/17 19:15 | Alessandro Giannessi v Christopher O'Connell | 7-6,6-3 |
| Challenger San Benedetto | 2019/07/16 10:00 | Christopher O'Connell v Riccardo Balzerani | 7-5,6-3 |
| ITF M25 Casinalbo | 2019/07/14 15:00 | Christian Lindell v Christopher O'Connell | 7-6,5-7,6-3 |