Kei Nishikori defeated Roger Federer 3-6 7-5 6-4 in the Miami Masters quarter-final on hard. The upset overturned the form book — Roger Federer came in leading the head-to-head 8–2. Kei Nishikori narrowed the head-to-head to 8–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-07-01 | Wimbledon | QF | grass | Roger Federer | 4-6 6-1 6-4 6-4 |
| 2018-11-12 | Tour Finals | RR | hard | Kei Nishikori | 7-6(4) 6-3 |
| 2018-10-29 | Paris Masters | QF | hard | Roger Federer | 6-4 6-4 |
| 2018-10-08 | Shanghai Masters | QF | hard | Roger Federer | 6-4 7-6(4) |
| 2017-01-16 | Australian Open | R16 | hard | Roger Federer | 6-7(4) 6-4 6-1 4-6 6-3 |
| 2015-11-15 | Tour Finals | RR | hard | Roger Federer | 7-5 4-6 6-4 |
| 2014-11-09 | Tour Finals | RR | hard | Roger Federer | 6-3 6-2 |
| 2014-06-09 | Halle | SF | grass | Roger Federer | 6-3 7-6(4) |
| 2013-05-05 | Madrid Masters | R16 | clay | Kei Nishikori | 6-4 1-6 6-2 |
| 2011-10-31 | Basel | F | hard | Roger Federer | 6-1 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
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