| Challenger Newport Beach Qual | 01/21 20:25 | 46 | Dennis Novikov v Raymond Sarmiento | 7-5,6-1 | |
| Challenger Newport Beach Qual | 01/20 20:00 | 45 | Dennis Novikov v Kaichi Uchida | 6-1,3-6,7-6 | |
| Australian Open Qual | 01/11 07:10 | 45 | Dennis Novikov v Elias Ymer | 7-6,3-6,3-6 | |
| Australian Open Qual | 01/10 00:55 | 44 | Marinko Matosevic v Dennis Novikov | 3-6,6-7 | |
| Challenger Noumea | 01/02 00:30 | 25 | Alejandro Gonzalez v Dennis Novikov | 6-7,6-3,6-4 | |
| Challenger Knoxville | 11/08 15:00 | 25 | [281] Mats Moraing v Dennis Novikov [225] | 6-4,6-2 | |
| Challenger Charlottesville | 10/31 14:00 | 25 | [113] Cameron Norrie v Dennis Novikov [226] | 6-3,6-1 | |
| Challenger Las Vegas | 10/16 21:15 | 25 | [231] Evan King v Dennis Novikov [217] | 6-7,7-6,6-4 | |
| Challenger Fairfield | 10/10 17:00 | 25 | Axel Geller v Dennis Novikov | Cancelled | |
| Challenger Monterrey | 10/03 18:00 | 25 | [429] Bradley Klahn v Dennis Novikov [217] | Retired | |
| Challenger Tiburon | 09/26 17:00 | 25 | Dennis Novikov v Tennys Sandgren | Cancelled | |
| Challenger Columbus | 09/23 16:20 | 28 | Dennis Novikov v Alexander Ward | 1-6,3-6 | |
| Challenger Columbus | 09/22 18:25 | 27 | [126] Quentin Halys v Dennis Novikov [225] | 1-6,6-2,4-6 | |
| Challenger Columbus | 09/21 16:00 | 26 | [282] Austin Krajicek v Dennis Novikov [225] | 4-6,3-6 | |
| Challenger Columbus | 09/19 16:55 | 25 | [379] Matthew Barton v Dennis Novikov [225] | 7-5,1-6,3-6 | |
| Challenger Cary | 09/14 17:35 | 26 | [338] Facundo Mena v Dennis Novikov [206] | 6-4,6-3 | |
| Challenger Cary | 09/13 23:50 | 25 | [281] Austin Krajicek v Dennis Novikov [206] | 6-4,5-7,5-7 | |
| US Open Qual | 08/24 15:00 | 45 | [208] Dennis Novikov v Maximilian Marterer [124] | 6-3,5-7,3-6 | |
| US Open Qual | 08/22 19:45 | 44 | [208] Dennis Novikov v Yasutaka Uchiyama [188] | 6-3,2-6,7-5 | |
| Challenger Aptos | 08/11 18:00 | 27 | [216] Dennis Novikov v Alexander Bublik [125] | 1-6,4-6 | |
| Challenger Aptos | 08/10 20:00 | 26 | [101] Mikhail Kukushkin v Dennis Novikov [216] | 7-6,6-7,3-6 | |
| Challenger Aptos | 08/08 18:00 | 25 | [188] Gleb Sakharov v Dennis Novikov [216] | 4-6,4-6 | |
| ATP Los Cabos | 08/01 02:40 | 25 | [219] Dennis Novikov v Matthew Ebden [154] | 6-1,3-6,3-6 | |
| ATP Atlanta Qual | 07/23 18:45 | 46 | [133] Quentin Halys v Dennis Novikov [203] | 6-7,7-5,6-4 | |
| ATP Atlanta Qual | 07/22 20:00 | 45 | [441] Ante Pavic v Dennis Novikov [203] | 4-6,3-6 | |
| ATP Newport | 07/21 17:00 | 27 | [21] John Isner v Dennis Novikov [203] | 6-4,6-4 | |
| ATP Newport | 07/19 20:55 | 26 | [203] Dennis Novikov v Frank Dancevic [422] | 6-3,6-2 | |
| ATP Newport | 07/17 15:00 | 25 | [203] Dennis Novikov v Marco Chiudinelli [211] | 6-1,6-3 | |
| Challenger Winnetka | 07/11 19:45 | 25 | Dennis Novikov v Dennis Nevolo | 2-6,4-6 | |
| Wimbledon Qual | 06/29 13:10 | - | [182] Nicolas Jarry v Dennis Novikov [175] | 4-6,6-3,6-4,6-4 |