Tomas Berdych advanced when Milos Raonic retired 5-2 in the Monte Carlo Masters quarter-final. Tomas Berdych narrowed the head-to-head to 6–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-06-11 | Stuttgart | QF | grass | Milos Raonic | 7-6 7-6 |
| 2017-05-22 | Lyon | SF | clay | Tomas Berdych | 7-6 7-6 |
| 2017-05-15 | Rome Masters | R16 | clay | Milos Raonic | 6-3 6-2 |
| 2016-03-07 | Indian Wells Masters | R16 | hard | Milos Raonic | 6-4 7-6 |
| 2014-10-27 | Paris Masters | SF | hard | Milos Raonic | 6-3 3-6 7-5 |
| 2013-10-28 | Paris Masters | R16 | hard | Tomas Berdych | 7-6 6-4 |
| 2013-09-23 | Bangkok | F | hard | Milos Raonic | 7-6 6-3 |
| 2012-08-12 | Cincinnati Masters | R16 | hard | Milos Raonic | 6-4 2-6 6-2 |
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
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About