Kei Nishikori defeated Milos Raonic 7-6 7-6 in the Madrid Masters round of 16 on clay. The result followed the form book — Kei Nishikori came in leading the head-to-head 4–2, defending last year's quarter-final. Kei Nishikori extended the head-to-head to 5–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2015-03-06 | Davis Cup WG R1: CAN vs JPN | RR | hard | Kei Nishikori | 3-6 6-3 6-4 2-6 6-4 |
| 2015-01-04 | Brisbane | SF | hard | Milos Raonic | 6-7(4) 7-6(4) 7-6(4) |
| 2014-09-29 | Tokyo | F | hard | Kei Nishikori | 7-6(5) 4-6 6-4 |
| 2014-08-25 | US Open | R16 | hard | Kei Nishikori | 4-6 7-6(4) 6-7(6) 7-5 6-4 |
| 2014-06-23 | Wimbledon | R16 | grass | Milos Raonic | 4-6 6-1 7-6(4) 6-3 |
| 2012-10-01 | Tokyo | F | hard | Kei Nishikori | 7-6(5) 3-6 6-0 |
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