| No. of times Played | 12 |
|
|
|
| Win % | 100% |
| H2H |
| Last Played | 2021 | First Played | 2013 |
| Tournament | Australian Open | Tournament | SRB vs.CAN WG SF |
| Round | Round of 16 | Round | Round Robin |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 67 | Score | 67 |
| No. of times Played | 10 |
|
|
|
| Win % | 80% |
| H2H |
| Last Played | 2019 | First Played | 2010 |
| Tournament | Laver Cup | Tournament | Tokyo |
| Round | Round Robin | Round | Round of 16 |
| Winner | Rafael Nadal | Winner | Rafael Nadal |
| Score | 36 67 | Score | 46 46 |
| No. of times Played | 15 |
|
|
|
| Win % | 80% |
| H2H |
| Last Played | 2018 | First Played | 2012 |
| Tournament | ATP Masters 1000 Paris | Tournament | Halle |
| Round | Round of 32 | Round | Quarter-Finals |
| Winner | Roger Federer | Winner | Roger Federer |
| Score | (W/O) | Score | 76 |
| No. of times Played | 16 |
|
|
|
| Win % | 69% |
| H2H |
| Last Played | 2020 | First Played | 2012 |
| Tournament | ATP Masters 1000 Cincinnati | Tournament | Tokyo |
| Round | Round of 16 | Round | Semi-Finals |
| Winner | Milos Raonic | Winner | Milos Raonic |
| Score | 62 62 | Score | 63 67 |
| No. of times Played | 5 |
|
|
|
| Win % | 20% |
| H2H |
| Last Played | 2019 | First Played | 2016 |
| Tournament | ATP Masters 1000 Canada | Tournament | Australian Open |
| Round | Round of 64 | Round | Round of 128 |
| Winner | Milos Raonic | Winner | Milos Raonic |
| Score | 64 64 | Score | 61 64 64 |
