| 2019-11-20 | Davis Cup Finals RR: SRB vs JPN | Hard | RR | 2 |  Novak Djokovic | 73 |  Yoshihito Nishioka | 6-1 6-2 | H2H | 3 | 67 | 0 | 1 | 62.5% | 48.9% | 37.0% | 8/13 |
| 2019-11-21 | Davis Cup Finals RR: FRA vs SRB | Hard | RR | 2 | Novak Djokovic | 24 |  Benoit Paire | 6-3 6-3 | H2H | 3 | 69 | 6 | 5 | 62.7% | 67.6% | 36.4% | 3/6 |
| 2019-11-22 | Davis Cup Finals QF: SRB vs RUS | Hard | RR | 2 | Novak Djokovic | 17 |  Karen Khachanov | 6-3 6-3 | H2H | 3 | 74 | 4 | 1 | 64.8% | 62.9% | 47.4% | 1/4 |
| 2019-11-11 | Tour Finals | Hard | RR | 2 | Novak Djokovic (2) | 8 |  Matteo Berrettini (8) | 6-2 6-1 | H2H | 3 | 63 | 4 | 1 | 60.0% | 75.0% | 75.0% | 0/1 |
| 2019-11-11 | Tour Finals | Hard | RR | 5 |  Dominic Thiem (5) | 2 | Novak Djokovic (2) | 6-7(5) 6-3 7-6(5) | H2H | 3 | 167 | 6 | 4 | 56.8% | 67.6% | 51.9% | 6/9 |
| 2019-11-11 | Tour Finals | Hard | RR | 3 |  Roger Federer (3) | 2 | Novak Djokovic (2) | 6-4 6-3 | H2H | 3 | 73 | 12 | 2 | 73.5% | 80.6% | 69.2% | 1/1 |
| 2019-10-28 | Paris Masters | Hard | SF | 1 | Novak Djokovic (1) | 27 |  Grigor Dimitrov | 7-6(5) 6-4 | H2H | 3 | 98 | 5 | 4 | 64.5% | 85.0% | 63.6% | 0/0 |
| 2019-10-28 | Paris Masters | Hard | QF | 1 | Novak Djokovic (1) | 7 |  Stefanos Tsitsipas (7) | 6-1 6-2 | H2H | 3 | 58 | 5 | 0 | 69.0% | 79.3% | 76.9% | 0/0 |
| 2019-10-28 | Paris Masters | Hard | R16 | 1 | Novak Djokovic (1) | 75 |  Kyle Edmund | 7-6(7) 6-1 | H2H | 3 | 82 | 6 | 1 | 66.7% | 88.9% | 55.6% | 0/0 |
| 2019-10-28 | Paris Masters | Hard | R32 | 1 | Novak Djokovic (1) | 97 | Corentin Moutet (LL) | 7-6(2) 6-4 | H2H | 3 | 106 | 4 | 3 | 68.4% | 71.2% | 58.3% | 4/6 |
