Stadium: Court 7 Round: 26 Ground: Hardcourt indoor
| Challenger Tallahassee | 2016/04/26 16:10 | Tim Smyczek v Brian Baker | 4-6,5-7 |
| Challenger Winnipeg | 2016/07/11 15:00 | Tim Smyczek v Kevin Kylar | 6-1,6-1 |
| Wimbledon Qual | 2016/06/22 12:15 | Tim Smyczek v Hiroki Moriya | 1-6,6-3,4-6 |
| Wimbledon Qual | 2016/06/20 18:05 | Tim Smyczek v Ilya Ivashka | 7-6,6-2 |
| French Open Qual | 2016/05/16 15:25 | Tim Smyczek v Adrian Ungur | 2-6,7-6,3-6 |
| Challenger Bordeaux | 2016/05/09 15:00 | Tim Smyczek v Quentin Halys | 2-6,3-6 |
| Challenger Tallahassee | 2016/04/26 16:10 | Tim Smyczek v Brian Baker | 4-6,5-7 |
| Challenger Savannah | 2016/04/20 00:00 | Tim Smyczek v Frances Tiafoe | 4-6,2-6 |
| Challenger Sarasota | 2016/04/12 21:00 | Frances Tiafoe v Tim Smyczek | 6-4,6-3 |
| ATP Newport | 2016/07/13 17:15 | Brian Baker v Marcos Baghdatis | 4-6,3-6 |
| ATP Newport | 2016/07/12 16:20 | Brian Baker v Austin Krajicek | 6-2,3-6,6-2 |
| ATP Newport Qual | 2016/07/11 16:25 | Brydan Klein v Brian Baker | 6-7,4-6 |
| Wimbledon | 2016/06/27 10:30 | Marin Cilic v Brian Baker | 6-3,7-5,6-3 |
| ATP Halle | 2016/06/14 10:00 | Brian Baker v Florian Mayer | 5-7,6-7 |
| French Open | 2016/05/24 09:00 | Bernard Tomic v Brian Baker | 6-3,6-4,6-4 |
| Challenger Tallahassee | 2016/04/27 23:35 | Brian Baker v Noah Rubin | 5-7,7-6,2-6 |
| Challenger Tallahassee | 2016/04/26 16:10 | Tim Smyczek v Brian Baker | 4-6,5-7 |