Stadium: Court 1 Round: 28 Ground: Hardcourt outdoor
| Challenger Cary | 2016/09/14 17:00 | Novikov, Dennis v Klein, Brydan | 6-4,6-4 |
| Challenger Winnipeg | 2019/07/10 16:55 | Klein, Brydan v Darian King | 0-6,6-7 |
| Challenger Winnipeg | 2019/07/08 17:50 | Klein, Brydan v Saraiva, Bernardo | 6-1,6-2 |
| Ilkley, Great Britain | 2019/06/19 15:05 | Klein, Brydan v Ymer, Mikael | 3-6,1-6 |
| Ilkley, Great Britain | 2019/06/18 13:20 | Jan Choinski v Klein, Brydan | 6-2,5-7,2-6 |
| Ilkley, Great Britain | 2019/06/17 11:00 | Evgeny Karlovskiy v Klein, Brydan | 6-4,1-6,2-6 |
| Challenger - Nottingham | 2019/06/11 14:40 | Ryan Peniston v Klein, Brydan | 4-6,6-4,6-4 |
| Challenger - Nottingham | 2019/06/10 13:35 | Klein, Brydan v Glasspool, Lloyd | 7-6,6-2 |
| Surbiton, Great Britain | 2019/06/05 11:50 | Klein, Brydan v Schnur, Brayden | 3-6,3-6 |
| Challenger Winnipeg | 2019/07/10 18:50 | Novikov, Dennis v Schnur, Brayden | 0-6,6-7 |
| Challenger Winnipeg | 2019/07/08 17:50 | Novikov, Dennis v Peck, Joshua | 6-4,7-6 |
| Challenger Columbus | 2019/06/12 20:00 | Young, Donald v Novikov, Dennis | 6-7,2-6 |
| Challenger Columbus | 2019/06/11 16:30 | Novikov, Dennis v Redlicki, Michael | 6-4,6-3 |
| Challenger - Savannah | 2019/04/30 14:00 | Novikov, Dennis v Manuel Guinard | 3-6,6-4,4-6 |
| Challenger - Tallahassee | 2019/04/22 23:25 | Novikov, Dennis v Emilio Gomez | 4-6,2-6 |
| Drummondville, Canada | 2019/03/13 01:45 | Novikov, Dennis v Maden, Yannick | 4-6,1-6 |
| Drummondville, Canada | 2019/03/11 21:40 | Novikov, Dennis v Andrea Collarini | 6-4,6-4 |