Grigor Dimitrov (Bulgaria) 2 - 5 Alex de Minaur (Australia)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 11 Apr 2025 |
Monte-Carlo Rolex Masters
Monte-Carlo,
Monaco
ATP Tour Masters, Clay |
Q |
Alex de Minaur
(AUS  )
|
0-6 0-6 |
| 17 Feb 2024 |
ABN Amro
Rotterdam,
The Netherlands
ATP Tour 500, Hard |
SF |
Alex de Minaur
(AUS )
|
4-6 4-6 |
| 20 Apr 2023 |
Barcelona Open Banc Sabadell
Barcelona,
Spain
ATP Tour 500, Clay |
R16 |
Alex de Minaur
(AUS )
|
w.o. |
| 17 Feb 2023 |
ABN Amro
Rotterdam,
The Netherlands
ATP Tour 500, Hard |
Q |
Grigor Dimitrov
(BUL  )
|
6-3 3-6 7-6(6) |
| 10 Aug 2022 |
National Bank Open
Toronto/Montreal,
Canada
ATP Tour Masters, Hard |
R32 |
Alex de Minaur
(AUS )
|
6-7(4) 5-7 |
| 24 Oct 2020 |
European Open
Antwerp,
Belgium
ATP Tour 250, Hard |
SF |
Alex de Minaur
(AUS )
|
6-7(4) 7-6(3) 4-6 |
| 01 Sep 2019 |
US Open
Flushing Meadows, NY,
USA
Grand Slam, Hard |
R16 |
Grigor Dimitrov
(BUL )
|
7-5 6-3 6-4 |