Nick Kyrgios defeated Milos Raonic 7-6 6-3 in the Rome Masters round of 32 on clay. The upset overturned the form book — Milos Raonic came in leading the head-to-head 4–2. Nick Kyrgios narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-01-14 | Australian Open | R128 | hard | Milos Raonic | 6-4 7-6(5) 6-4 |
| 2016-06-13 | Queen's Club | R32 | grass | Milos Raonic | 6-7(5) 6-4 6-4 |
| 2016-03-21 | Miami Masters | QF | hard | Nick Kyrgios | 6-4 7-6(4) |
| 2015-06-29 | Wimbledon | R32 | grass | Nick Kyrgios | 5-7 7-5 7-6(3) 6-3 |
| 2014-06-23 | Wimbledon | QF | grass | Milos Raonic | 6-7(4) 6-2 6-4 7-6(4) |
| 2014-05-26 | Roland Garros | R128 | clay | Milos Raonic | 6-3 7-6(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