Grigor Dimitrov (Bulgaria) 2 - 1 Brandon Nakashima (USA)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 25 Mar 2025 |
Miami Open
Miami, Florida,
USA
ATP Tour Masters, Hard |
R16 |
Grigor Dimitrov
(BUL  )
|
6-4 7-5 |
| 01 Sep 2022 |
US Open
Flushing Meadows, NY,
USA
Grand Slam, Hard |
R64 |
Brandon Nakashima
(USA )
|
6-7(5) 5-7 3-6 |
| 10 May 2022 |
Internazionali BNL d'Italia
Rome,
Italy
ATP Tour Masters, Clay |
R64 |
Grigor Dimitrov
(BUL )
|
6-3 6-4 |