| Wimbledon | 07/01 12:50 | 24 | [153] Dennis Novak v Jason Kubler [99] | 3-6,4-6,4-6 | |
| Wimbledon | 06/28 16:45 | 23 | [153] Dennis Novak v Facundo Bagnis [102] | 7-6,2-6,6-4,6-3 | |
| Wimbledon | 06/23 10:00 | 19 | [107] Stefan Kozlov v Dennis Novak [155] | 5-7,4-6,7-5,6-3,3-6 | |
| Wimbledon | 06/22 10:00 | 19 | [211] Federico Gaio v Dennis Novak [155] | 2-6,3-6 | |
| Wimbledon | 06/20 12:00 | 14 | [232] Jonas Forejtek v Dennis Novak [155] | 6-7,1-6 | |
| Challenger Blois | 06/16 12:10 | 26 | [147] Dennis Novak v Genaro Alberto Olivieri [222] | 2-6,4-6 | |
| Challenger Blois | 06/14 13:00 | 25 | Dennis Novak v Terence Atmane | 6-4,7-6 | |
| Challenger Bratislava | 06/08 11:45 | 26 | [237] Alexander Shevchenko v Dennis Novak [154] | 6-3,6-2 | |
| Challenger Bratislava | 06/06 12:25 | 25 | [262] Nicolas Moreno De Alboran v Dennis Novak [154] | 1-6,3-6 | |
| Challenger Prostejov | 05/30 14:30 | 25 | [150] Dennis Novak v Matheus P De Almeida [225] | Retired | |
| French Open | 05/16 11:40 | 14 | [205] Lorenzo Giustino v Dennis Novak [150] | 7-5,7-6 | |
| Challenger Mauthausen | 05/07 13:35 | 28 | [148] Dennis Novak v Jiri Lehecka [88] | 2-6,3-6 |