| 2019-11-20 | Davis Cup Finals RR: BEL vs AUS | Hard | RR | 30 |  Nick Kyrgios | 158 |  Steve Darcis | 6-2 7-6(9) | H2H | 3 | 86 | 4 | 1 | 52.8% | 89.5% | 47.1% | 2/4 |
| 2019-11-19 | Davis Cup Finals RR: AUS vs COL | Hard | RR | 30 | Nick Kyrgios | 470 |  Alejandro Gonzalez | 6-4 6-4 | H2H | 3 | 71 | 16 | 1 | 78.3% | 88.9% | 80.0% | 0/0 |
| 2019-09-23 | Zhuhai | Hard | R32 | 74 |  Andreas Seppi | 27 | Nick Kyrgios (6) | 7-6(5) 6-1 | H2H | 3 | 64 | 8 | 3 | 63.8% | 83.8% | 52.4% | 0/1 |
| 2019-09-20 | Laver Cup | Hard | RR | 3 |  Roger Federer | 27 | Nick Kyrgios | 6-7(5) 7-5 1-0(7) | H2H | 3 | - | - | - | - | - | - | - |
| 2019-08-26 | US Open | Hard | R32 | 43 |  Andrey Rublev | 30 | Nick Kyrgios (28) | 7-6(5) 7-6(5) 6-3 | H2H | 5 | 111 | 12 | 1 | 56.6% | 83.9% | 74.4% | 2/2 |
| 2019-08-26 | US Open | Hard | R64 | 30 | Nick Kyrgios (28) | 104 |  Antoine Hoang | 6-4 6-2 6-4 | H2H | 5 | 118 | 24 | 1 | 70.0% | 69.6% | 75.0% | 3/5 |
| 2019-08-26 | US Open | Hard | R128 | 30 | Nick Kyrgios (28) | 86 |  Steve Johnson | 6-3 7-6(1) 6-4 | H2H | 5 | 122 | 24 | 8 | 59.5% | 88.0% | 55.9% | 3/4 |
| 2019-08-12 | Cincinnati Masters | Hard | R32 | 9 | Karen Khachanov (8) | 27 | Nick Kyrgios | 6-7(3) 7-6(4) 6-2 | H2H | 3 | 133 | 13 | 3 | 68.4% | 83.1% | 56.7% | 3/4 |
| 2019-08-12 | Cincinnati Masters | Hard | R64 | 27 | Nick Kyrgios | 47 | Lorenzo Sonego | 7-5 6-4 | H2H | 3 | 79 | 4 | 1 | 57.4% | 93.5% | 73.9% | 0/0 |
| 2019-08-05 | Canada Masters | Hard | R64 | 33 |  Kyle Edmund | 27 | Nick Kyrgios | 6-3 6-4 | H2H | 3 | 67 | 15 | 3 | 66.7% | 91.7% | 50.0% | 0/0 |
