| ATP - Kitzbuhel | 07/27 13:40 | 25 | [74] Gianluca Mager v Dennis Novak [124] | 6-4,6-0 | |
| ATP Gstaad | 07/22 08:30 | 26 | [14] Casper Ruud v Dennis Novak [124] | 6-4,7-6 | |
| ATP Gstaad | 07/20 08:30 | 25 | [170] Kacper Zuk v Dennis Novak [124] | 4-6,4-6 | |
| ATP Gstaad | 07/20 08:00 | 25 | Yannick Hanfmann v Dennis Novak | CANC | |
| ATP - Bastad | 07/13 09:00 | 25 | [122] Dennis Novak v Pedro Martinez [95] | 5-7,1-6 | |
| ATP - Bastad | 07/12 09:00 | 19 | [122] Dennis Novak v Marc-Andrea Huesler [157] | 6-2,6-2 | |
| ATP - Bastad | 07/11 10:55 | 14 | [122] Dennis Novak v Viktor Durasovic [373] | 6-2,6-4 | |
| Challenger - Salzburg | 07/05 16:05 | 25 | [159] Blaz Rola v Dennis Novak [122] | 7-5,7-6 | |
| Wimbledon | 06/30 15:30 | 23 | [74] Steve Johnson v Dennis Novak [122] | 7-6,6-2,7-5 | |
| ATP - Halle | 06/13 11:40 | 19 | [93] Ricardas Berankis v Dennis Novak [111] | 6-4,6-3 | |
| ATP - Halle | 06/12 11:20 | 14 | [202] Yannick Maden v Dennis Novak [111] | Retired | |
| ATP - Stuttgart | 06/08 09:00 | 19 | [111] Dennis Novak v Altug Celikbilek [239] | 6-1,6-7,5-7 |