Head to head
3
Hard
1
0
Clay
1
Grigor Dimitrov's wins on the left · Milos Raonic's on the right · bar lengths share one scale
All meetings (7)
| 2020 | Antwerp | Hard | QF | Grigor Dimitrov | W/O |
| 2018 | Madrid Masters | Clay | R32 | Milos Raonic | 7-5 3-6 6-3 |
| 2017 | Brisbane | Hard | SF | Grigor Dimitrov | 7-6(7) 6-2 |
| 2016 | Beijing | Hard | SF | Grigor Dimitrov | W/O |
| 2014 | Australian Open | Hard | R32 | Grigor Dimitrov | 6-3 3-6 6-4 7-6(10) |
| 2012 | Brisbane | Hard | R16 | Grigor Dimitrov | 6-3 6-4 |
| 2011 | Stockholm | Hard | QF | Milos Raonic | 7-5 6-4 |
Methodology
Head-to-head totals and surface splits exclude walkovers (no match was played), which follows ATP convention — walkover meetings still appear in the match list. The momentum chart plots the running lead across all counted meetings, oldest to newest.