Grigor Dimitrov and Karen Khachanov have met 4 times, with Grigor Dimitrov leading the head-to-head 3–1. Below is every meeting with scores and the full match history — open any row for set-by-set detail.
| Grigor Dimitrov | Karen Khachanov | |
|---|---|---|
| Tour | ATP | ATP |
| Rank | #137 | #50 |
| Country | BUL | — |
| Age | 35 | 30 |
| Height | 1.91 m | 1.98 m |
| Plays | right-handed | right-handed |
| Year | Tournament | Surface | Round | Winner | Score | Match |
|---|---|---|---|---|---|---|
| 2025 | Miami | Hard | R32 | Grigor Dimitrov | 6(3)-7(7), 6-4, 7-5 | match → |
| 2025 | Miami Open | Hard | R32 | Grigor Dimitrov | 6(3)-7(7), 6-4, 7-5 | match → |
| 2024 | Paris Masters | Hard | Quarterfinal | Karen Khachanov | 6-2, 6-3 | match → |
| 2023 | Shanghai Masters | Hard | R32 | Grigor Dimitrov | 7(8)-6(6), 6-4 | match → |
Grigor Dimitrov won the most recent meeting 6(3)-7(7), 6-4, 7-5 at the Miami 2025 (R32). Over their last 4 meetings, Grigor Dimitrov leads 3–1. Recent-winner sequence (1=Grigor Dimitrov, 2=Karen Khachanov): 1121.
Grigor Dimitrov leads the head-to-head 3–1 across 4 meetings.
Grigor Dimitrov and Karen Khachanov have played 4 times.
Grigor Dimitrov won their most recent meeting 6(3)-7(7), 6-4, 7-5 at the Miami 2025.
Their first meeting was at the Shanghai Masters 2023, won by Grigor Dimitrov 7(8)-6(6), 6-4.
More: Grigor Dimitrov · Karen Khachanov · Grigor Dimitrov head-to-heads · Karen Khachanov head-to-heads