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 Charlottesville | 2016/11/01 20:50 | Tim Smyczek v Thai-Son Kwiatkowski | 6-4,2-6,6-3 |
| Challenger Fairfield | 2016/10/12 21:20 | Joris De Loore v Tim Smyczek | 6-4,7-6 |
| Challenger Fairfield | 2016/10/10 19:00 | Denis Shapovalov v Tim Smyczek | 2-6,4-6 |
| Challenger Stockton | 2016/10/05 17:00 | Mackenzie McDonald v Tim Smyczek | 6-4,6-4 |
| Challenger Stockton | 2016/10/04 19:35 | Grega Zemlja v Tim Smyczek | 4-6,6-3,1-6 |
| Challenger Tiburon | 2016/10/01 22:45 | Tim Smyczek v Michael Mmoh | 6-2,3-6,6-7 |
| Challenger Tiburon | 2016/09/30 19:20 | Mitchell Krueger v Tim Smyczek | 2-6,4-6 |
| Challenger Tiburon | 2016/09/28 22:00 | Sam Groth v Tim Smyczek | 5-7,6-7 |
| Challenger Charlottesville | 2016/11/01 14:00 | Brian Baker v Tim Van Rijthoven | 6-4,6-2 |
| Challenger Fairfield | 2016/10/13 19:00 | Brian Baker v Santiago Giraldo | 4-6,7-5,4-6 |
| Challenger Fairfield | 2016/10/11 23:00 | Mackenzie McDonald v Brian Baker | 3-6,4-6 |
| Challenger Stockton | 2016/10/05 18:40 | Denis Kudla v Brian Baker | 5-7,6-4,7-5 |
| Challenger Stockton | 2016/10/03 23:15 | Peter Polansky v Brian Baker | 6-7,6-3,5-7 |
| Challenger Tiburon | 2016/09/29 18:00 | Brian Baker v Dennis Novikov | 4-6,6-3,1-6 |
| Challenger Tiburon | 2016/09/27 17:00 | Brian Baker v Austin Krajicek | 6-4,6-3 |
| US Open | 2016/08/29 18:30 | Brian Baker v Federico Delbonis | 6-3,7-6,4-6,2-6,2-6 |