Stadium: Court 2 Round: 44 Ground: Grass
| Challenger Poznan | 2018/06/05 09:00 | Henri Laaksonen v Jason Kubler | 6-4,6-2 |
| French Open | 2019/05/30 12:05 | Novak Djokovic v Henri Laaksonen | 6-1,6-4,6-3 |
| French Open | 2019/05/27 12:35 | Henri Laaksonen v Pedro Martinez | 6-1,6-0,7-6 |
| French Open | 2019/05/24 08:00 | Henri Laaksonen v Mikael Ymer | 1-6,6-2,2-6 |
| French Open | 2019/05/22 13:55 | Henri Laaksonen v Facundo Arguello | 4-6,6-4,6-3 |
| French Open | 2019/05/20 10:20 | Henri Laaksonen v Daniel Brands | 6-3,6-0 |
| Challenger Rome | 2019/05/12 10:00 | Gian Marco Moroni v Henri Laaksonen | 7-6,6-7,2-6 |
| Challenger Rome | 2019/05/11 13:25 | Henri Laaksonen v Paolo Lorenzi | 7-6,6-7,6-1 |
| Challenger Rome | 2019/05/10 11:30 | Salvatore Caruso v Henri Laaksonen | 4-6,4-6 |
| Challenger Nottingham | 2019/06/11 17:15 | Tatsuma Ito v Jason Kubler | 6-4,6-4 |
| Challenger Surbiton | 2019/06/05 10:45 | Jason Kubler v Denis Kudla | 2-6,3-6 |
| Challenger Surbiton | 2019/06/03 12:35 | Jason Kubler v Liam Broady | 4-6,6-2,6-0 |
| French Open | 2019/05/22 14:00 | Viktor Troicki v Jason Kubler | 6-1,7-6 |
| French Open | 2019/05/20 08:00 | Jason Kubler v Ramkumar Ramanathan | 6-4,6-4 |
| Challenger Nanchang | 2019/04/23 07:30 | Jason Kubler v Ben Patael | 1-6,6-4,5-7 |
| Challenger Anning | 2019/04/18 03:00 | James Duckworth v Jason Kubler | 7-5,7-6 |
| Challenger Anning | 2019/04/16 03:25 | Makoto Ochi v Jason Kubler | 2-6,1-6 |