Kei Nishikori defeated Richard Gasquet 7-6 6-1 in the Tokyo semi-final on hard. The upset overturned the form book — Richard Gasquet came in ranked #673, leading the head-to-head 8–2, defending last year's quarter-final, but Kei Nishikori had been the form player, winning 2 of their last 4 on hard. 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) |
| 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 |
| 2016-05-02 | Madrid Masters | R16 | clay | Kei Nishikori | 6-4 7-5 |
| 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 |
Averages from each player's recent completed matches (20 vs 19). ATP, WTA & Challenger.