Tim Smyczek advanced when Donald Young retired 6-2 3-0 in the Acapulco qualifying round 2. Tim Smyczek narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-07-31 | Washington | R64 | hard | Donald Young | 4-6 6-3 6-4 |
| 2017-07-24 | Atlanta | R32 | hard | Donald Young | 6-4 6-2 |
| 2016-08-01 | Atlanta | R16 | hard | Donald Young | 4-6 7-6(1) 6-3 |
| 2016-04-04 | Houston | R16 | clay | Tim Smyczek | 6-2 6-4 |
| 2016-02-15 | Delray Beach | R16 | hard | Tim Smyczek | 1-6 7-6(2) 6-2 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Young D.: 2 days rest · 1 match, 21 games (7d). Higher means fresher. About