Grigor Dimitrov (Bulgaria) 5 - 2 Jan-Lennard Struff (Germany)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 24 Mar 2023 |
Miami Open
Miami, Florida,
USA
ATP Tour Masters, Hard |
R64 |
Grigor Dimitrov
(BUL  )
|
4-6 7-6(5) 6-4 |
| 12 Apr 2021 |
Monte-Carlo Rolex Masters
Monte-Carlo,
Monaco
ATP Tour Masters, Clay |
R64 |
Grigor Dimitrov
(BUL )
|
6-3 6-4 |
| 13 May 2019 |
Internazionali BNL d'Italia
Rome,
Italy
ATP Tour Masters, Clay |
R64 |
Jan-Lennard Struff
(GER  )
|
4-6 7-6(5) 3-6 |
| 17 Apr 2019 |
Monte-Carlo Rolex Masters
Monte-Carlo,
Monaco
ATP Tour Masters, Clay |
R32 |
Grigor Dimitrov
(BUL )
|
7-6(2) 6-4 |
| 19 Apr 2017 |
Monte-Carlo Rolex Masters
Monte-Carlo,
Monaco
ATP Tour Masters, Clay |
R32 |
Jan-Lennard Struff
(GER )
|
6-4 3-6 2-6 |
| 17 Oct 2013 |
Stockholm Open
Stockholm,
Sweden
ATP Tour 250, Hard |
R16 |
Grigor Dimitrov
(BUL )
|
6-1 6-3 |
| 01 Aug 2010 |
Apano Cup
Dortmund,
Germany
Futures, Clay |
F |
Grigor Dimitrov
(BUL )
|
7-5 7-5 |