Both players have only dropped one set during their time in Milan.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Next Gen ATP Finals Final Stage
|
Final | Stefanos Tsitsipas |
2-4
4-1 4-3 4-3 |
| 2018 |
Next Gen ATP Finals Final Stage
|
Semi Finals | Alex De Minaur |
3-4
4-1 4-1 3-4 4-2 |
| 2018 |
Next Gen ATP Finals, Group B
|
Championship | Alex De Minaur |
4-3
4-1 4-2 |
| 2018 |
Next Gen ATP Finals, Group B
|
Championship | Alex De Minaur |
4-1
3-4 4-1 4-2 |
| 2018 |
Rolex Paris Masters
|
1/32 | Feliciano Lopez |
6-7
6-4 7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
WTA Elite Trophy Camellia Group
|
Championship | Garbine Muguruza |
7-6
2-6 6-7 |
| 2018 |
WTA Elite Trophy Camellia Group
|
Championship | Anastasija Sevastova |
6-0
7-6 |
| 2018 |
VTB Kremlin Cup
|
Semi Finals | Ons Jabeur |
6-3
3-6 6-3 |
| 2018 |
VTB Kremlin Cup
|
Quarter Finals | Anastasija Sevastova |
4-6
7-5 6-3 |
| 2018 |
VTB Kremlin Cup
|
1/8 | Anastasija Sevastova |
7-5
4-6 6-4 |
| 2018 |
VTB Kremlin Cup
|
1/16 | Anastasija Sevastova |
4-6
7-5 6-3 |
| 2018 |
China Open
|
Final | Caroline Wozniacki |
3-6
3-6 |
| 2018 |
China Open
|
Semi Finals | Anastasija Sevastova |
6-4
6-4 |
| 2018 |
China Open
|
Quarter Finals | Anastasija Sevastova |
6-3
7-6 |
| 2018 |
China Open
|
1/8 | Anastasija Sevastova |
3-6
2-6 |
| 2018 |
China Open
|
1/16 | Anastasija Sevastova | |
| 2018 |
China Open
|
1/32 | Anastasija Sevastova |
6-4
6-2 |
