Round: 25 Ground: Hardcourt outdoor
| 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 |
| Challenger Milan Qual | 2016/06/18 09:05 | James McGee v Eduardo Dischinger | 6-2,6-1 |
| Challenger Blois Qual | 2016/06/13 14:00 | James McGee v Juan Pablo Paz | 4-6,0-6 |
| ATP Washington Qual | 2016/07/17 16:55 | Ryan Harrison v Amir Weintraub | 6-4,6-3 |
| ATP Washington Qual | 2016/07/16 16:40 | Ryan Shane v Amir Weintraub | 4-6,2-6 |
| ATP Newport | 2016/07/12 17:00 | Amir Weintraub v Yuichi Sugita | 6-4,3-6,2-6 |
| ATP Newport Qual | 2016/07/11 15:00 | Amir Weintraub v Frank Dancevic | 6-7,7-6,4-6 |
| ATP Newport Qual | 2016/07/10 16:00 | Amir Weintraub v Evan King | 7-6,7-6 |
| Wimbledon Qual | 2016/06/21 13:50 | Ruben Bemelmans v Amir Weintraub | 6-3,6-2 |
| French Open Qual | 2016/05/17 11:10 | Jordi Samper-Montana v Amir Weintraub | 6-2,3-6,6-2 |
| ITF Turkey F15 | 2016/04/12 07:00 | Amir Weintraub v Matteo Herrmann-Zunic | 6-3,2-6,6-2 |