
Grigor Dimitrov advanced when Donald Young retired 6-4 3-0 in the Madrid Masters round of 64. Grigor Dimitrov extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-02-22 | Acapulco | R16 | hard | Grigor Dimitrov | 6-3 6-4 |
| 2014-08-04 | Canada Masters | R32 | hard | Grigor Dimitrov | 4-6 6-2 6-3 |
| 2012-05-27 | Roland Garros | R128 | clay | Grigor Dimitrov | 7-6 6-1 6-1 |
| 2012-02-20 | Memphis | R32 | hard | Donald Young | 7-6 4-6 7-6 |
| 2011-08-21 | Winston-Salem | R32 | hard | Grigor Dimitrov | 6-4 2-6 7-6 |
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
Dimitrov G.: 7 days rest · 1 match, 18 games (7d) · Young D.: 2 days rest · 2 matches, 52 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About