Round: 28 Ground: Hardcourt outdoor
| Challenger Dallas | 2016/02/02 16:30 | James McGee v Dennis Novikov | 5-7,6-1,6-4 |
| 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 |
| French Open Qual | 2016/05/18 13:20 | Marco Trungelliti v Dennis Novikov | 7-5,3-6,7-5 |
| Challenger Granby | 2016/08/04 16:00 | Vincent Millot v James McGee | 6-3,1-6,4-6 |
| Challenger Granby | 2016/08/02 21:10 | James McGee v Amir Weintraub | 6-3,6-3 |
| Challenger Granby Qual | 2016/08/01 16:15 | James McGee v Erik Crepaldi | 6-1,6-4 |
| Challenger Granby Qual | 2016/07/31 16:30 | James McGee v Raleigh Smith | 6-4,6-3 |
| Challenger Winnipeg | 2016/07/14 19:45 | Peter Polansky v James McGee | 6-4,6-1 |
| Challenger Winnipeg | 2016/07/12 19:35 | Nicolas Meister v James McGee | 2-6,2-6 |
| Challenger Winnipeg Qual | 2016/07/10 16:45 | James McGee v Luke Bambridge | 6-4,6-4 |
| Challenger Milan Qual | 2016/06/19 09:30 | James McGee v Nicolas Jarry | 4-6,6-7 |