Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2019/07/10 16:55 | Brydan Klein v Darian King | 0-6,6-7 |
| Challenger Winnipeg | 2019/07/08 17:50 | Brydan Klein v Bernardo Saraiva | 6-1,6-2 |
| Challenger Ilkley | 2019/06/19 15:05 | Brydan Klein v Mikael Ymer | 3-6,1-6 |
| Challenger Ilkley | 2019/06/18 13:20 | Jan Choinski v Brydan Klein | 6-2,5-7,2-6 |
| Challenger Ilkley | 2019/06/17 11:00 | Evgeny Karlovskiy v Brydan Klein | 6-4,1-6,2-6 |
| Challenger Nottingham | 2019/06/11 14:40 | Ryan Peniston v Brydan Klein | 4-6,6-4,6-4 |
| Challenger Nottingham | 2019/06/10 13:35 | Brydan Klein v Lloyd Glasspool | 7-6,6-2 |
| Challenger Surbiton | 2019/06/05 11:50 | Brydan Klein v Brayden Schnur | 3-6,3-6 |
| Wimbledon | 2019/06/24 15:05 | Steven Diez v Tatsuma Ito | 6-4,6-1 |
| Challenger Ilkley | 2019/06/18 10:00 | Tatsuma Ito v Ruben Bemelmans | 7-6,3-6,4-6 |
| Challenger Nottingham | 2019/06/14 11:00 | Tatsuma Ito v Lukas Rosol | 4-6,7-6,3-6 |
| Challenger Nottingham | 2019/06/13 12:00 | Marcel Granollers v Tatsuma Ito | 3-6,5-7 |
| Challenger Nottingham | 2019/06/11 17:15 | Tatsuma Ito v Jason Kubler | 6-4,6-4 |
| French Open | 2019/05/20 08:00 | Tatsuma Ito v Johan Sebastien Tatlot | 2-6,6-7 |
| Challenger Busan | 2019/05/10 05:00 | Yasutaka Uchiyama v Tatsuma Ito | 4-6,6-0,6-3 |
| Challenger Busan | 2019/05/09 04:40 | Tatsuma Ito v Cem Ilkel | 7-5,6-7,6-4 |