Round: 24 Ground: Hardcourt outdoor
| 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 |
| ITF China F6 | 2016/05/11 02:00 | James Duckworth v Wishaya Trongcharoenchaikul | 6-4,6-3 |
| 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 |
| 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 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 |