

Grigor Dimitrov defeated Stan Wawrinka 6-4 6-4 in the Acapulco quarter-final on hard. The upset overturned the form book — Stan Wawrinka came in ranked #117, leading the head-to-head 7–5, defending last year's quarter-final. Grigor Dimitrov narrowed the head-to-head to 7–6.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-05-08 | Rome Masters | R64 | clay | Grigor Dimitrov | 6-4 7-6(3) |
| 2019-08-12 | Cincinnati Masters | R64 | hard | Stan Wawrinka | 5-7 6-4 7-6(4) |
| 2019-08-05 | Canada Masters | R64 | hard | Stan Wawrinka | 6-4 6-4 |
| 2019-05-27 | Roland Garros | R32 | clay | Stan Wawrinka | 7-6(5) 7-6(4) 7-6(8) |
| 2018-08-27 | US Open | R128 | hard | Stan Wawrinka | 6-3 6-2 7-5 |
| 2018-07-02 | Wimbledon | R128 | grass | Stan Wawrinka | 1-6 7-6(3) 7-6(5) 6-4 |
| 2016-08-15 | Cincinnati Masters | R16 | hard | Grigor Dimitrov | 6-4 6-4 |
| 2015-05-03 | Madrid Masters | R16 | clay | Grigor Dimitrov | 7-6(5) 3-6 6-3 |
| 2015-04-12 | Monte Carlo Masters | R16 | clay | Grigor Dimitrov | 6-1 6-2 |
| 2014-06-09 | Queen's Club | SF | grass | Grigor Dimitrov | 6-2 6-4 |
| 2013-05-05 | Madrid Masters | R16 | clay | Stan Wawrinka | 3-6 6-4 6-1 |
| 2011-01-17 | Australian Open | R64 | hard | Stan Wawrinka | 7-5 6-3 6-3 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the hard field, opponent-adjusted over 52 weeks). About
Averages over each player's completed matches in the selected window (200 vs 198). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Dimitrov G.: 8 days rest · 4 matches (14d) · Wawrinka S.: 14 days rest · 1 match (14d). Higher means fresher. About