Rafael Nadal defeated Milos Raonic 6-3 7-6 in the Shanghai Masters round of 16 on hard. The result followed the form book — Rafael Nadal came in leading the head-to-head 7–2, defending last year's round of 32. Rafael Nadal extended the head-to-head to 8–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-09-20 | Laver Cup | RR | hard | Rafael Nadal | 6-3 7-6(1) |
| 2017-01-16 | Australian Open | QF | hard | Rafael Nadal | 6-4 7-6(7) 6-4 |
| 2017-01-02 | Brisbane | QF | hard | Milos Raonic | 4-6 6-3 6-4 |
| 2015-03-12 | Indian Wells Masters | QF | hard | Milos Raonic | 4-6 7-6(10) 7-5 |
| 2014-03-19 | Miami Masters | QF | hard | Rafael Nadal | 4-6 6-2 6-4 |
| 2013-08-05 | Canada Masters | F | hard | Rafael Nadal | 6-2 6-2 |
| 2013-04-22 | Barcelona | SF | clay | Rafael Nadal | 6-4 6-0 |
| 2011-10-03 | Tokyo | R16 | hard | Rafael Nadal | 7-5 6-3 |
| 2010-10-04 | Tokyo | R16 | hard | Rafael Nadal | 6-4 6-4 |
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.