Tsitsipas made a sold transition to clay against a fellow Australian Open semifinalist.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Davis Cup Finals, Final Stage
|
Championship | Rafael Nadal |
3-6
6-7 |
| 2019 |
Rolex Paris Masters
|
Semi Finals | Denis Shapovalov | |
| 2018 |
Internazionali BNL d'Italia
|
1/8 | Rafael Nadal |
6-4
6-1 |
| 2017 |
Coupe Rogers
|
1/8 | Denis Shapovalov |
6-3
4-6 6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Australian Open ATP
|
Quarter Finals | Stefanos Tsitsipas |
3-6
2-6 7-6 6-4 7-5 |
| 2021 |
Australian Open ATP
|
1/8 | Rafael Nadal |
3-6
4-6 2-6 |
| 2021 |
Australian Open ATP
|
1/16 | Rafael Nadal |
5-7
2-6 5-7 |
| 2021 |
Australian Open ATP
|
1/32 | Rafael Nadal |
1-6
4-6 2-6 |
| 2021 |
Australian Open ATP
|
1/64 | Rafael Nadal |
3-6
4-6 1-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Miami Open
|
1/16 | Hubert Hurkacz |
3-6
6-7 |
| 2021 |
Miami Open
|
1/32 | Denis Shapovalov |
6-7
6-4 6-4 |
| 2021 |
Dubai Tennis Championships
|
Semi Finals | Lloyd Harris |
6-7
6-4 7-6 |
| 2021 |
Dubai Tennis Championships
|
Quarter Finals | Denis Shapovalov |
7-5
6-4 |
| 2021 |
Dubai Tennis Championships
|
1/8 | Denis Shapovalov |
6-4
6-3 |
| 2021 |
Dubai Tennis Championships
|
1/16 | Denis Shapovalov |
6-1
6-3 |
| 2021 |
Qatar Open
|
Quarter Finals | Taylor Fritz |
5-7
6-3 7-5 |
| 2021 |
Qatar Open
|
1/8 | Denis Shapovalov |
5-7
4-6 |
