The Greek will hope to avenge his heartbreaking loss to Djokovic at the 2020 French Open.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Internazionali BNL d'Italia
|
1/16 | Petra Martic |
7-5
6-3 |
| 2021 |
Internazionali BNL d'Italia
|
1/32 | Kristina Mladenovic |
6-3
6-4 |
| 2021 |
Internazionali BNL d'Italia, Qualification
|
1/8 | Vera Zvonareva |
2-6
5-7 |
| 2021 |
Madrid Open
|
1/32 | Belinda Bencic |
4-6
2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Internazionali BNL d'Italia
|
1/8 | Novak Djokovic |
6-2
6-1 |
| 2021 |
Internazionali BNL d'Italia
|
1/16 | Novak Djokovic |
6-3
7-6 |
| 2021 |
Serbia Open
|
Semi Finals | Aslan Karatsev |
5-7
6-4 4-6 |
| 2021 |
Serbia Open
|
Quarter Finals | Novak Djokovic |
6-1
6-3 |
| 2021 |
Monte Carlo Masters
|
1/8 | Daniel Evans |
4-6
5-7 |
| 2021 |
Monte Carlo Masters
|
1/16 | Novak Djokovic |
6-4
6-2 |
