Estadio: Center Court Round: 24 Ground: Clay
| Challenger de Poznan | 2019/06/05 09:50 | Gianluca Mager v Christopher Heyman | 7-6,6-4 |
| Challenger de Poznan | 2019/06/03 11:30 | Mats Moraing v Christopher Heyman | 3-6,5-7 |
| ITF M25 Gyula | 2019/05/31 10:50 | Christopher Heyman v Markus Eriksson | 3-6,6-2,6-7 |
| ITF M25 Gyula | 2019/05/30 09:50 | Christopher Heyman v Joao Lucas Reis da Silva | 6-3,6-4 |
| ITF M25 Gyula | 2019/05/29 11:35 | Christopher Heyman v Tristan Meraut | 3-6,6-3,6-4 |
| ITF 15 Antalya | 2019/05/26 07:45 | Ergi Kirkin v Christopher Heyman | 4-6,3-6 |
| ITF 15 Antalya | 2019/05/25 07:45 | Niklas Guttau v Christopher Heyman | 5-7,2-6 |
| ITF 15 Antalya | 2019/05/24 07:45 | Denis Klok v Christopher Heyman | 1-6,6-7 |
| ITF M15 Kaltenkirchen | 2019/06/12 13:45 | Jacob Grills v Cedrik-Marcel Stebe | 4-6,6-4,1-6 |
| ITF M15 Kaltenkirchen | 2019/06/11 17:25 | Jacob Grills v Matheus P De Almeida | 5-7,7-6,7-6 |
| Challenger de Poznan | 2019/06/03 09:55 | Jacob Grills v Zdenek Kolar | 1-6,3-6 |
| ITF M25 Most | 2019/05/30 10:25 | Ondrej Krstev v Jacob Grills | 2-6,6-4,6-3 |
| ITF M25 Most | 2019/05/29 08:00 | Jiri Barnat v Jacob Grills | 3-6,2-6 |
| ITF M25 Jablonec Nad Nisou | 2019/05/23 11:30 | Patrik Rikl v Jacob Grills | 6-1,2-6,6-3 |
| Challenger de Samarcanda | 2019/05/14 05:00 | Jacob Grills v Dmitry Popko | 3-6,6-7 |
| Challenger de Shymkent | 2019/05/07 05:40 | Andrej Martin v Jacob Grills | 6-0,6-2 |