Stadium: Court 15 Round: 25 Ground: Grass
| Challenger Happy Valley | 2017/01/03 00:30 | Young, Donald v Bemelmans, Ruben | 4-6,6-2,6-7 |
| Wimbledon, London, Great Britain | 2019/06/26 10:00 | Bemelmans, Ruben v Akira Santillan | 6-7,6-3,12-10 |
| Wimbledon, London, Great Britain | 2019/06/24 11:40 | Elias Ymer v Bemelmans, Ruben | 3-6,7-6,4-6 |
| Ilkley, Great Britain | 2019/06/20 14:55 | Bemelmans, Ruben v Antoine Hoang | 1-6,1-6 |
| Ilkley, Great Britain | 2019/06/19 18:35 | Evgeny Karlovskiy v Bemelmans, Ruben | 4-6,1-6 |
| Ilkley, Great Britain | 2019/06/18 10:00 | Tatsuma Ito v Bemelmans, Ruben | 7-6,3-6,4-6 |
| Challenger - Nottingham | 2019/06/15 13:20 | Bemelmans, Ruben v Antoine Hoang | 3-6,4-6 |
| Challenger - Nottingham | 2019/06/14 15:30 | Maden, Yannick v Bemelmans, Ruben | 6-4,3-6,4-6 |
| Challenger - Nottingham | 2019/06/12 19:25 | Bemelmans, Ruben v Ramkumar Ramanathan | 6-1,6-0 |
| Wimbledon, London, Great Britain | 2019/06/26 10:00 | Young, Donald v Daniel Elahi Galan | 7-6,6-3 |
| Wimbledon, London, Great Britain | 2019/06/24 14:20 | Young, Donald v Egor Gerasimov | 6-4,7-6 |
| Challenger Columbus | 2019/06/12 20:00 | Young, Donald v Novikov, Dennis | 6-7,2-6 |
| Little Rock, USA | 2019/06/05 16:35 | Young, Donald v Zhizhen Zhang | 4-6,6-3,3-6 |
| French Open, Paris, France | 2019/05/20 08:00 | Marcos Giron v Young, Donald | 6-0,6-1 |
| Puerto Vallarta, Mexico | 2019/05/01 18:00 | Sarkissian, Alexander v Young, Donald | 1-6,7-6,6-2 |
| Challenger Leon | 2019/04/24 16:00 | Escobar, Gonzalo v Young, Donald | 6-3,7-5 |
| Monterrey, Mexico | 2019/04/06 21:35 | Emilio Gomez v Young, Donald | 2-6,6-3,6-4 |