| No. of times Played | 9 |
|
|
|
| Win % | 44% |
| H2H |
| Last Played | 2021 | First Played | 2017 |
| Tournament | US Open | Tournament | Eastbourne |
| Round | Finals | Round | Semi-Finals |
| Winner | Daniil Medvedev | Winner | Novak Djokovic |
| Score | 46 46 46 | Score | 64 64 |
| No. of times Played | 10 |
|
|
|
| Win % | 30% |
| H2H |
| Last Played | 2021 | First Played | 2017 |
| Tournament | US Open | Tournament | ATP Masters 1000 Rome |
| Round | Semi-Finals | Round | Finals |
| Winner | Novak Djokovic | Winner | Alexander Zverev |
| Score | 46 62 64 46 62 | Score | 46 36 |
| No. of times Played | 8 |
|
|
|
| Win % | 25% |
| H2H |
| Last Played | 2021 | First Played | 2018 |
| Tournament | Roland Garros | Tournament | ATP Masters 1000 Canada |
| Round | Finals | Round | Round of 16 |
| Winner | Novak Djokovic | Winner | Stefanos Tsitsipas |
| Score | 67 | Score | 36 76 |
| No. of times Played | 58 |
|
|
|
| Win % | 48% |
| H2H |
| Last Played | 2021 | First Played | 2006 |
| Tournament | Roland Garros | Tournament | Roland Garros |
| Round | Semi-Finals | Round | Quarter-Finals |
| Winner | Novak Djokovic | Winner | Rafael Nadal |
| Score | 36 63 76 | Score | 46 46 (RET) |
| No. of times Played | 4 |
|
|
|
| Win % | 0% |
| H2H |
| Last Played | 2021 | First Played | 2019 |
| Tournament | US Open | Tournament | Nitto ATP Finals |
| Round | Quarter-Finals | Round | Round Robin |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 57 62 62 63 | Score | 62 61 |
| No. of times Played | 7 |
|
|
|
| Win % | 0% |
| H2H |
| Last Played | 2021 | First Played | 2019 |
| Tournament | Wimbledon | Tournament | ATP Cup |
| Round | Semi-Finals | Round | Quarter-Finals |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 76 | Score | 46 61 76 |
| No. of times Played | 6 |
|
|
|
| Win % | 0% |
| H2H |
| Last Played | 2020 | First Played | 2014 |
| Tournament | Nitto ATP Finals | Tournament | US Open |
| Round | Round Robin | Round | Round of 128 |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 63 62 | Score | 61 62 64 |
| No. of times Played | 2 |
|
|
|
| Win % | 50% |
| H2H |
| Last Played | 2021 | First Played | 2021 |
| Tournament | Belgrade | Tournament | Belgrade |
| Round | Semi-Finals | Round | Semi-Finals |
| Winner | Aslan Karatsev | Winner | Aslan Karatsev |
| Score | 57 64 46 | Score | 57 64 46 |
| No. of times Played | 51 |
|
|
|
| Win % | 45% |
| H2H |
| Last Played | 2020 | First Played | 2006 |
| Tournament | Australian Open | Tournament | SUI v. SCG WG PO |
| Round | Semi-Finals | Round | Round Robin |
| Winner | Novak Djokovic | Winner | Roger Federer |
| Score | 76 | Score | 36 26 36 |
| No. of times Played | 12 |
|
|
|
| Win % | 42% |
| H2H |
| Last Played | 2020 | First Played | 2014 |
| Tournament | Nitto ATP Finals | Tournament | ATP Masters 1000 Shanghai |
| Round | Semi-Finals | Round | Round of 32 |
| Winner | Dominic Thiem | Winner | Novak Djokovic |
| Score | 57 76 | Score | 63 64 |
| No. of times Played | 22 |
|
|
|
| Win % | 9% |
| H2H |
| Last Played | 2021 | First Played | 2010 |
| Tournament | US Open | Tournament | Roland Garros |
| Round | Round of 32 | Round | Round of 64 |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 67 | Score | 61 64 64 |
| No. of times Played | 1 |
|
|
|
| Win % | 0% |
| H2H |
| Last Played | 2021 | First Played | 2021 |
| Tournament | Roland Garros | Tournament | Roland Garros |
| Round | Round of 16 | Round | Round of 16 |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 67 | Score | 67 |
| No. of times Played | 12 |
|
|
|
| Win % | 17% |
| H2H |
| Last Played | 2021 | First Played | 2008 |
| Tournament | Wimbledon | Tournament | ATP Masters 1000 Miami |
| Round | Round of 64 | Round | Round of 64 |
| Winner | Novak Djokovic | Winner | Kevin Anderson |
| Score | 63 63 63 | Score | 67 |
| No. of times Played | 36 |
|
|
|
| Win % | 31% |
| H2H |
| Last Played | 2017 | First Played | 2006 |
| Tournament | Doha | Tournament | ATP Masters 1000 Madrid |
| Round | Finals | Round | Round of 16 |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 63 57 64 | Score | 16 75 63 |
| No. of times Played | 11 |
|
|
|
| Win % | 18% |
| H2H |
| Last Played | 2019 | First Played | 2008 |
| Tournament | ATP Masters 1000 Cincinnati | Tournament | ATP Masters 1000 Monte Carlo |
| Round | Round of 32 | Round | Quarter-Finals |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 75 61 | Score | 64 60 |
| No. of times Played | 12 |
|
|
|
| Win % | 0% |
| 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 | 76 | Score | 76 |
| No. of times Played | 2 |
|
|
|
| Win % | 100% |
| H2H |
| Last Played | 2017 | First Played | 2017 |
| Tournament | ATP Masters 1000 Indian Wells | Tournament | ATP Masters 1000 Indian Wells |
| Round | Round of 16 | Round | Round of 16 |
| Winner | Nick Kyrgios | Winner | Nick Kyrgios |
| Score | 46 67 | Score | 46 67 |
| No. of times Played | 26 |
|
|
|
| Win % | 23% |
| H2H |
| Last Played | 2019 | First Played | 2004 |
| Tournament | US Open | Tournament | Aachen |
| Round | Round of 16 | Round | Round of 32 |
| Winner | Stan Wawrinka | Winner | Novak Djokovic |
| Score | 46 57 12 (RET) | Score | 62 63 |
| No. of times Played | 20 |
|
|
|
| Win % | 20% |
| H2H |
| Last Played | 2019 | First Played | 2007 |
| Tournament | ATP Masters 1000 Rome | Tournament | US Open |
| Round | Quarter-Finals | Round | Round of 32 |
| Winner | Novak Djokovic | Winner | Novak Djokovic |
| Score | 46 76 | Score | 61 63 64 |
