The Serb finished off Grigor Dimitrov in the afternoon, and he beat Milos Raonic later on.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Davis Cup Playoff
|
Championship | Milos Raonic |
6-3
6-2 6-2 |
| 2018 |
US Open ATP
|
1/8 | John Isner |
3-6
6-3 6-4 3-6 6-2 |
| 2018 |
US Open ATP
|
1/16 | Milos Raonic |
7-6
6-4 6-3 |
| 2018 |
US Open ATP
|
1/32 | Milos Raonic |
6-3
6-4 6-4 |
| 2018 |
US Open ATP
|
1/64 | Milos Raonic |
7-6
6-4 1-6 6-3 |
| 2018 |
Western & Southern Open
|
Quarter Finals | Novak Djokovic |
5-7
6-4 3-6 |
| 2018 |
Western & Southern Open
|
1/8 | Milos Raonic |
7-6
6-4 |
| 2018 |
Western & Southern Open
|
1/16 | Milos Raonic |
3-6
5-7 |
| 2018 |
Western & Southern Open
|
1/32 | Milos Raonic |
3-6
3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
Roland Garros, Qualification WTA
|
1/24 (Special Qual) | Ivana Jorovic |
4-6
4-6 |
| 2016 |
Roland Garros, Qualification WTA
|
1/48 (Special Qual) | Mathilde Johansson |
5-7
1-6 |
| 2016 |
Grand Prix SAR La Princesse Lalla Meryem, Qualification
|
1/16 | Aryna Sabalenka |
6-3
7-6 |
