Grigor Dimitrov (Bulgaria) 1 - 1 Matteo Berrettini (Italy)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 23 Oct 2019 |
Erste Bank Open 500
Vienna,
Austria
ATP Tour 500, Hard |
R16 |
Matteo Berrettini
(ITA  )
|
6-7(5) 6-7(1) |
| 14 Apr 2019 |
Monte-Carlo Rolex Masters
Monte-Carlo,
Monaco
ATP Tour Masters, Clay |
R64 |
Grigor Dimitrov
(BUL  )
|
7-5 6-4 |