Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Sao Bras Alportel | 2019/09/08 09:30 | Fred Gil v Simon Freund | 6-4,4-6,6-1 |
| ITF M15 Sao Bras Alportel | 2019/09/07 09:30 | Simon Freund v Julius Tverijonas | 6-2,6-0 |
| ITF M15 Sao Bras Alportel | 2019/09/06 09:00 | Simon Freund v Anton Matusevich | 7-5,6-4 |
| ITF M15 Sao Bras Alportel | 2019/09/05 09:00 | Marek Gengel v Simon Freund | 2-6,1-6 |
| ITF M15 Sao Bras Alportel | 2019/09/03 10:00 | Tomas Luis v Simon Freund | 1-6,1-6 |
| ITF M15 Ystad | 2019/08/07 08:15 | Simon Freund v Juan Manuel Cerundolo | 2-6,6-7 |
| ITF - M15 Pittsburgh | 2019/07/07 15:00 | Alexander Cozbinov v Simon Freund | 2-6,6-2,6-1 |
| ITF - M15 Pittsburgh | 2019/07/06 17:00 | Paul Oosterbaan v Simon Freund | 1-6,1-6 |
| ITF M15 Burgas | 2019/10/11 12:15 | Peter Nagy v Kai Wehnelt | 6-2,6-3 |
| ITF M15 Burgas | 2019/10/11 08:30 | Stefan Micov v Kai Wehnelt | 2-6,4-6 |
| ITF M15 Burgas | 2019/10/10 07:00 | Nini Gabriel Dica v Kai Wehnelt | 1-6,7-6,2-6 |
| ITF M15 Burgas | 2019/10/08 14:30 | Nini Gabriel Dica v Kai Wehnelt | 1-6,7-6,2-6 |
| ITF - M15 Antalya | 2019/10/03 07:00 | Alejandro H Franco v Kai Wehnelt | 2-6,7-5,6-2 |
| ITF - M15 Antalya | 2019/10/02 08:55 | Kelsey Stevenson v Kai Wehnelt | 0-6,2-6 |
| ITF - M15 Antalya | 2019/09/27 08:10 | Kai Wehnelt v Marsel Ilhan | 1-6,3-6 |
| ITF - M15 Antalya | 2019/09/26 13:15 | Kai Wehnelt v Mats Hermans | 6-1,3-6,7-6 |