Stadium: Court 1 Round: 28 Ground: Hardcourt outdoor
| Challenger Cary | 2016/09/14 17:00 | Dennis Novikov v Brydan Klein | 6-4,6-4 |
| 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 |
| Challenger Winnipeg | 2019/07/10 18:50 | Dennis Novikov v Brayden Schnur | 0-6,6-7 |
| Challenger Winnipeg | 2019/07/08 17:50 | Dennis Novikov v Joshua Peck | 6-4,7-6 |
| Challenger Columbus | 2019/06/12 20:00 | Donald Young v Dennis Novikov | 6-7,2-6 |
| Challenger Columbus | 2019/06/11 16:30 | Dennis Novikov v Michael Redlicki | 6-4,6-3 |
| Challenger Savannah | 2019/04/30 14:00 | Dennis Novikov v Manuel Guinard | 3-6,6-4,4-6 |
| Challenger Tallahassee | 2019/04/22 23:25 | Dennis Novikov v Emilio Gomez | 4-6,2-6 |
| Challenger Drummondville | 2019/03/13 01:45 | Dennis Novikov v Yannick Maden | 4-6,1-6 |
| Challenger Drummondville | 2019/03/11 21:40 | Dennis Novikov v Andrea Collarini | 6-4,6-4 |