James Duckworth 7-5,6-1 Tim Smyczek 2016-07-18 20:00
Round: 24 Ground: Hardcourt outdoor
Home History
| ATP Washington Qual | 2016/07/17 14:00 | James Duckworth v Alexander Sarkissian | 4-6,7-6,6-2 |
| ATP Washington Qual | 2016/07/16 17:20 | James Duckworth v Ulises Blanch | 6-1,6-4 |
| ATP Newport | 2016/07/12 16:25 | James Duckworth v Adrian Mannarino | 7-6,6-7,6-7 |
| Wimbledon Qual | 2016/06/21 09:30 | James Duckworth v Kenny de Schepper | 1-6,7-6,3-6 |
| ITF China F6 | 2016/05/15 02:00 | James Duckworth v Yusuke Takahashi | 6-3,6-2 |
| ITF China F6 | 2016/05/14 02:00 | James Duckworth v Raymond Sarmiento | 6-7,6-1,6-3 |
| ITF China F6 | 2016/05/13 04:10 | James Duckworth v Rigele Te | 7-5,6-3 |
| ITF China F6 | 2016/05/12 03:55 | James Duckworth v Fajing Sun | 6-3,6-1 |
Away History
| Challenger Winnipeg | 2016/07/14 15:35 | Tim Smyczek v Daniel Nguyen | 2-6,3-6 |
| 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 |