Round: 24 Ground: Hardcourt outdoor
| Challenger Knoxville | 2015/11/13 17:45 | Dennis Novikov v James Duckworth | 7-5,6-4 |
| Challenger Knoxville | 2015/11/12 18:50 | Sekou Bangoura v James Duckworth | 6-4,3-6,4-6 |
| Challenger Knoxville | 2015/11/10 16:30 | Frederik Nielsen v James Duckworth | 6-7,4-6 |
| US Open | 2015/09/01 21:15 | Hyeon Chung v James Duckworth | 6-3,6-1,6-2 |
| ATP Cincinnati Qual | 2015/08/15 20:25 | Steve Johnson v James Duckworth | 7-5,6-4 |
| ATP Montreal Qual | 2015/08/09 20:45 | Denis Kudla v James Duckworth | 6-4,6-1 |
| ATP Montreal Qual | 2015/08/08 19:10 | Illya Marchenko v James Duckworth | 3-6,5-7 |
| ATP Washington | 2015/08/05 02:00 | James Duckworth v Kei Nishikori | 7-6,1-6,4-6 |
| 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 Houston | 2016/04/08 18:35 | Tim Smyczek v Feliciano Lopez | 2-6,3-6 |
| ATP Houston | 2016/04/07 18:00 | Donald Young v Tim Smyczek | 2-6,4-6 |
| ATP Houston | 2016/04/05 18:00 | Nicolas Kicker v Tim Smyczek | 6-4,6-7,4-6 |
| ATP Miami | 2016/03/28 22:00 | Tim Smyczek v Nick Kyrgios | 4-6,4-6 |
| ATP Miami | 2016/03/26 21:40 | John Isner v Tim Smyczek | 2-6,6-2,6-7 |