Kei Nishikori defeated Richard Gasquet 6-4 7-5 in the Madrid Masters round of 16 on clay. The upset overturned the form book — Richard Gasquet came in leading the head-to-head 8–2, defending last year's round of 32. Kei Nishikori narrowed the head-to-head to 8–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-08-05 | Canada Masters | R32 | hard | Richard Gasquet | 6-7(6) 6-2 7-6(4) |
| 2018-10-01 | Tokyo | SF | hard | Kei Nishikori | 7-6(2) 6-1 |
| 2016-05-23 | Roland Garros | R16 | clay | Richard Gasquet | 6-4 6-2 4-6 6-2 |
| 2016-05-09 | Rome Masters | R16 | clay | Kei Nishikori | 6-1 6-4 |
| 2015-11-02 | Paris Masters | R16 | hard | Richard Gasquet | 7-6(3) 4-1 RET |
| 2014-07-28 | Washington | QF | hard | Richard Gasquet | 6-1 6-4 |
| 2013-10-28 | Paris Masters | R16 | hard | Richard Gasquet | 6-3 6-2 |
| 2013-08-05 | Canada Masters | R16 | hard | Richard Gasquet | 1-6 6-3 6-3 |
| 2010-06-07 | Queen's Club | R64 | grass | Richard Gasquet | 6-3 6-3 |
| 2008-09-29 | Tokyo | R16 | hard | Richard Gasquet | 6-1 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 199). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About