Stadium: GRANDSTAND Round: 45 Ground: Hardcourt indoor
| ATP Washington Qual | 2016/07/16 14:00 | Scott Lipsky v Marinko Matosevic | 1-6,0-6 |
| WTA Kuala Lumpur Qual | 2014/09/21 05:50 | Scott Lipsky v Philipp Petzschner | 4-6,4-6 |
| WTA Kuala Lumpur Qual | 2014/09/20 04:30 | Muhammad-A B Z Abidin v Scott Lipsky | 3-6,3-6 |
| Challenger Knoxville | 2016/11/10 15:00 | Tim Smyczek v Michael Mmoh | 3-6,2-6 |
| Challenger Knoxville | 2016/11/09 16:20 | Tim Smyczek v Tim Van Rijthoven | 7-6,6-4 |
| Challenger Charlottesville | 2016/11/04 23:05 | Tim Smyczek v Ruben Bemelmans | 2-6,4-6 |
| Challenger Charlottesville | 2016/11/03 16:00 | Tim Smyczek v Brian Baker | 7-5,6-4 |
| 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 |