| ATP - Dubai | 02/29 15:00 | 29 | [1] Novak Djokovic v Stefanos Tsitsipas [6] | 6-3,6-4 | |
| ATP - Dubai | 02/28 15:00 | 28 | [1] Novak Djokovic v Gael Monfils [9] | 2-6,7-6,6-1 | |
| ATP - Dubai | 02/27 16:15 | 27 | [1] Novak Djokovic v Karen Khachanov [17] | 6-2,6-2 | |
| ATP - Dubai | 02/26 15:00 | 26 | [1] Novak Djokovic v Philipp Kohlschreiber [80] | 6-3,6-1 | |
| ATP - Dubai | 02/24 15:00 | 25 | [1] Novak Djokovic v Malek Jaziri [260] | 6-1,6-2 | |
| Open da Austrália | 02/02 08:30 | 29 | [5] Dominic Thiem v Novak Djokovic [2] | 4-6,6-4,6-2,3-6,4-6 | |
| Open da Austrália | 01/30 08:30 | 28 | [3] Roger Federer v Novak Djokovic [2] | 6-7,4-6,3-6 | |
| Open da Austrália | 01/28 08:00 | 27 | [35] Milos Raonic v Novak Djokovic [2] | 4-6,3-6,6-7 | |
| Open da Austrália | 01/26 03:35 | 26 | [14] Diego Schwartzman v Novak Djokovic [2] | 3-6,4-6,4-6 | |
| Open da Austrália | 01/24 04:40 | 25 | [71] Yoshihito Nishioka v Novak Djokovic [2] | 3-6,2-6,2-6 | |
| Open da Austrália | 01/22 03:25 | 24 | [146] Tatsuma Ito v Novak Djokovic [2] | 1-6,4-6,2-6 | |
| Open da Austrália | 01/20 10:00 | 23 | [37] Jan-Lennard Struff v Novak Djokovic [2] | 6-7,2-6,6-2,1-6 | |
| Taça ATP | 01/12 09:30 | 29 | [2] Novak Djokovic v Rafael Nadal [1] | 6-2,7-6 | |
| Taça ATP | 01/11 02:10 | 28 | [2] Novak Djokovic v Daniil Medvedev [5] | 6-1,5-7,6-4 | |
| Taça ATP | 01/10 01:05 | 27 | [2] Novak Djokovic v Denis Shapovalov [14] | 4-6,6-1,7-6 | |
| Taça ATP | 01/08 02:00 | 2 | [2] Novak Djokovic v Cristian Garin [33] | 6-3,6-3 | |
| Taça ATP | 01/06 10:00 | 2 | [2] Novak Djokovic v Gael Monfils [9] | 6-3,6-2 | |
| Taça ATP | 01/04 10:10 | 2 | [2] Novak Djokovic v Kevin Anderson [91] | 7-6,7-6 | |
| Mubadala World Tennis Championship | 12/21 13:00 | 29 | [2] Novak Djokovic v Karen Khachanov [17] | 7-5,6-3 | |
| Mubadala World Tennis Championship | 12/20 13:00 | 28 | [2] Novak Djokovic v Stefanos Tsitsipas [6] | 6-3,6-7,4-6 | |
| Taça Davis 2019 | 11/22 10:50 | - | [2] Novak Djokovic v Karen Khachanov [17] | 6-3,6-3 | |
| Taça Davis 2019 | 11/21 12:10 | 2 | [24] Benoit Paire v Novak Djokovic [2] | 3-6,3-6 | |
| Taça Davis 2019 | 11/20 11:40 | 2 | [2] Novak Djokovic v Yoshihito Nishioka [73] | 6-1,6-2 | |
| ATP - Finais do World Tour | 11/14 20:00 | 3 | [2] Novak Djokovic v Roger Federer [3] | 4-6,3-6 | |
| ATP - Finais do World Tour | 11/12 20:00 | 2 | [2] Novak Djokovic v Dominic Thiem [5] | 7-6,3-6,6-7 | |
| ATP - Finais do World Tour | 11/10 14:00 | 1 | [2] Novak Djokovic v Matteo Berrettini [8] | 6-2,6-1 | |
| ATP - Paris | 11/03 14:00 | 29 | [1] Novak Djokovic v Denis Shapovalov [28] | 6-3,6-4 | |
| ATP - Paris | 11/02 13:00 | 28 | [1] Novak Djokovic v Grigor Dimitrov [27] | 7-6,6-4 | |
| ATP - Paris | 11/01 14:50 | 27 | [1] Novak Djokovic v Stefanos Tsitsipas [7] | 6-1,6-2 | |
| ATP - Paris | 10/31 14:15 | 26 | [1] Novak Djokovic v Kyle Edmund [75] | 7-6,6-1 |