Round: 45 Ground: Hardcourt outdoor
| US Open Qual | 2016/08/23 21:50 | Dennis Novikov v Federico Gaio | 7-6,5-7,6-2 |
| ATP Washington Qual | 2016/07/17 15:40 | Dennis Novikov v Ernesto Escobedo | 6-7,4-6 |
| ATP Newport | 2016/07/13 15:00 | Dennis Novikov v Victor Estrella Burgos | 6-7,3-6 |
| Wimbledon | 2016/06/30 14:35 | Dennis Novikov v Joao Sousa | 4-6,4-6,6-3,4-6 |
| Wimbledon | 2016/06/28 10:30 | Luke Saville v Dennis Novikov | 6-4,4-6,5-7,4-6 |
| Wimbledon Qual | 2016/06/24 13:40 | Hiroki Moriya v Dennis Novikov | 6-2,2-6,3-6,2-6 |
| Wimbledon Qual | 2016/06/22 12:45 | Uladzimir Ignatik v Dennis Novikov | 6-2,6-7,8-10 |
| Wimbledon Qual | 2016/06/20 16:35 | Lloyd Glasspool v Dennis Novikov | 2-6,5-7 |
| US Open Qual | 2016/08/23 23:10 | Daniil Medvedev v Pedja Krstin | 6-7,6-7 |
| Challenger Poznan | 2016/07/15 10:15 | Ruben R. Hidalgo v Pedja Krstin | 6-3,6-1 |
| Challenger Poznan | 2016/07/12 13:30 | Hubert Hurkacz v Pedja Krstin | 2-6,6-0,4-6 |
| Wimbledon Qual | 2016/06/21 11:10 | Franko Skugor v Pedja Krstin | 6-2,6-4 |
| Challenger Caltanissetta | 2016/06/07 11:00 | Marcelo Arevalo v Pedja Krstin | 7-5,6-1 |
| French Open Qual | 2016/05/18 11:45 | Roberto Carballes Baena v Pedja Krstin | 6-4,6-2 |
| French Open Qual | 2016/05/16 08:00 | Pedja Krstin v Corentin Denolly | 7-5,6-3 |
| Challenger Bordeaux | 2016/05/10 08:00 | Jonathan Eysseric v Pedja Krstin | 7-6,7-5 |