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By surface
| Surface | Donald Young | Tim Smyczek |
| Hard |
3 |
1 |
| Clay |
0 |
1 |
All meetings (5)
| Date | Tour | Tournament | Round | Surface | Winner |
Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
| 2017-07-31 |
ATP |
Washington |
Round of 64 |
Hard |
Donald Young |
4-6 |
6-3 |
6-4 |
|
|
| 2017-07-24 |
ATP |
Atlanta |
Round of 32 |
Hard |
Donald Young |
6-4 |
6-2 |
|
|
|
| 2016-08-01 |
ATP |
Atlanta |
Round of 16 |
Hard |
Donald Young |
4-6 |
7-61 |
6-3 |
|
|
| 2016-04-04 |
ATP |
Houston |
Round of 16 |
Clay |
Tim Smyczek |
2-6 |
4-6 |
|
|
|
| 2016-02-15 |
ATP |
Delray Beach |
Round of 16 |
Hard |
Tim Smyczek |
6-1 |
6-72 |
2-6 |
|
|