| Wimbledon Qual | 06/28 15:15 | 45 | [175] Dennis Novikov v Stefan Kozlov [126] | 7-5,6-2 | |
| Wimbledon Qual | 06/26 13:05 | 44 | [175] Dennis Novikov v Di Wu [221] | 6-4,7-6 | |
| Challenger Ilkley | 06/20 13:00 | 25 | [173] Dennis Novikov v Quentin Halys [139] | 6-4,6-7,4-6 | |
| Challenger Ilkley Qual | 06/19 11:20 | 54 | [173] Dennis Novikov v Mackenzie McDonald [225] | 6-3,6-4 | |
| Challenger Ilkley Qual | 06/18 14:05 | 46 | [172] Dennis Novikov v Yannick Maden [203] | 6-7,6-0,6-4 | |
| Challenger Ilkley Qual | 06/17 16:25 | 45 | [172] Dennis Novikov v Joris De Loore [201] | 6-2,4-6,7-6 | |
| ATP Den Bosch | 06/12 13:10 | 25 | [82] Nicolas Mahut v Dennis Novikov [172] | 6-3,6-4 | |
| ATP Den Bosch Qual | 06/11 09:00 | 46 | [166] Jason Jung v Dennis Novikov [174] | 6-7,2-6 | |
| ATP Den Bosch Qual | 06/10 08:30 | 45 | [202] Ilya Ivashka v Dennis Novikov [174] | 5-7,6-7 | |
| Challenger Surbiton | 06/08 10:30 | 25 | Dennis Novikov v John Millman | 6-7,7-6,2-6 | |
| Challenger Surbiton Qual | 06/05 10:00 | 54 | [174] Dennis Novikov v Mackenzie McDonald [232] | 7-6,6-4 | |
| Challenger Surbiton Qual | 06/04 15:00 | 46 | [174] Dennis Novikov v Lukas Rosol [194] | 7-6,4-6,6-4 | |
| Challenger Surbiton Qual | 06/04 10:00 | 45 | [174] Dennis Novikov v Tim Puetz [465] | 6-7,6-2,6-4 | |
| French Open Qual | 05/24 14:05 | 45 | [174] Dennis Novikov v Roberto Quiroz [231] | 6-7,3-6 | |
| French Open Qual | 05/23 08:00 | 44 | [105] Henri Laaksonen v Dennis Novikov [174] | 2-6,3-6 | |
| Challenger Heilbronn | 05/16 14:00 | 25 | [174] Dennis Novikov v Lorenzo Giustino [186] | 4-6,4-6 | |
| Challenger Savannah | 05/05 21:30 | 27 | [393] Tommy Paul v Dennis Novikov [180] | 6-2,6-4 | |
| Challenger Savannah | 05/03 16:00 | 26 | Alejandro Gonzalez v Dennis Novikov | 7-5,4-6,3-6 | |
| Challenger Savannah | 05/02 16:10 | 25 | [180] Dennis Novikov v Peter Polansky [129] | 6-4,2-6,7-6 | |
| Challenger Tallahassee | 04/27 16:30 | 27 | [271] Blaz Rola v Dennis Novikov [191] | 6-1,6-2 | |
| Challenger Tallahassee | 04/26 16:20 | 26 | [191] Dennis Novikov v John-Patrick Smith [221] | 6-3,7-5 | |
| Challenger Tallahassee | 04/24 21:35 | 25 | [191] Dennis Novikov v Mackenzie McDonald [232] | 6-3,6-7,6-3 | |
| Challenger Sarasota | 04/18 00:20 | 25 | [74] Jared Donaldson v Dennis Novikov [189] | 6-2,6-4 | |
| ATP Houston Qual | 04/08 17:05 | 45 | [187] Dennis Novikov v Maximo Gonzalez [151] | 4-6,6-7 | |
| Challenger Leon | 03/29 02:20 | 25 | Victor E Burgos v Dennis Novikov | 4-6,7-6,6-0 | |
| Challenger Guadalajara | 03/22 20:00 | 25 | [214] Mirza Basic v Dennis Novikov [176] | 6-4,7-5 | |
| ATP Indian Wells Qual | 03/08 19:00 | 45 | [173] Dennis Novikov v Henri Laaksonen [123] | 6-4,4-6,0-6 | |
| ATP Indian Wells Qual | 03/07 19:00 | 44 | [69] Denis Istomin v Dennis Novikov [173] | Retired | |
| Challenger Morelos | 02/21 18:00 | 25 | Dennis Novikov v Austin Krajicek | 4-6,7-6,2-6 | |
| Challenger Tempe | 02/19 20:10 | 28 | Dennis Novikov v Tennys Sandgren | 6-4,4-6,3-6 |