The South African beat Djokovic before a Team World doubles win closed the gap to 7-5.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
Rogers Cup
Canada, Ontario, Toronto |
1/32 | Denis Shapovalov |
7-6
3-6 6-3 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
St. Petersburg Open
|
Quarter Finals | Martin Klizan |
6-3
5-7 3-6 |
| 2018 |
St. Petersburg Open
|
1/8 | Denis Shapovalov |
7-6
4-6 6-0 |
| 2018 |
St. Petersburg Open
|
1/16 | Denis Shapovalov |
7-6
6-2 |
| 2018 |
Davis Cup Playoff
|
Championship | Denis Shapovalov |
3-6
3-6 7-5 6-3 6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
US Open ATP
|
1/16 | Roger Federer |
4-6
1-6 5-7 |
| 2018 |
US Open ATP
|
1/32 | Nick Kyrgios |
4-6
7-6 6-3 6-0 |
| 2018 |
US Open ATP
|
1/64 | Nick Kyrgios |
7-5
2-6 6-4 6-2 |
| 2018 |
Western & Southern Open
|
1/8 | Juan Martin del Potro |
6-7
7-6 2-6 |
| 2018 |
Western & Southern Open
|
1/16 | Nick Kyrgios |
7-6
0-6 6-3 |
| 2018 |
Western & Southern Open
|
1/32 | Nick Kyrgios |
6-7
7-5 7-6 |
| 2018 |
Rogers Cup
|
1/32 | Stan Wawrinka |
1-6
7-5 7-5 |
