Winston Lin defeated Connor Smith 0-6 6-3 7-6 in the USA F7 round of 32 on clay. Winston Lin extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-10-10 | USA F31 | R16 | hard | Connor Smith | 6-2 7-6(4) |
| 2016-06-27 | USA F22 | QF | clay | Winston Lin | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.