| 2019-11-24 | Davis Cup Finals F: CAN vs ESP | Hard | RR | 9 |  Roberto Bautista Agut | 21 |  Felix Auger-Aliassime | 7-6(3) 6-3 | H2H | 3 | 109 | 4 | 6 | 52.9% | 77.8% | 46.9% | 3/5 |
| 2019-10-07 | Shanghai Masters | Hard | R32 | 7 |  Stefanos Tsitsipas (6) | 19 | Felix Auger-Aliassime | 7-6(3) 7-6(3) | H2H | 3 | 122 | 5 | 2 | 75.3% | 79.7% | 38.1% | 2/3 |
| 2019-10-07 | Shanghai Masters | Hard | R64 | 19 | Felix Auger-Aliassime | 54 |  Alexander Bublik (Q) | 7-6(5) 4-0 RET | H2H | 3 | 93 | 5 | 3 | 77.0% | 68.1% | 42.9% | 12/14 |
| 2019-09-30 | Beijing | Hard | R16 | 6 |  Alexander Zverev (2) | 20 | Felix Auger-Aliassime | 6-3 6-1 | H2H | 3 | 62 | 5 | 2 | 69.2% | 92.6% | 58.3% | 0/0 |
| 2019-09-30 | Beijing | Hard | R32 | 20 | Felix Auger-Aliassime | 44 | Albert Ramos-Vinolas (SE) | 6-3 6-4 | H2H | 3 | 80 | 11 | 3 | 66.7% | 91.2% | 58.8% | 1/1 |
| 2019-09-23 | Chengdu | Hard | R16 | 62 |  Joao Sousa | 20 | Felix Auger-Aliassime (2) | 6-4 6-7(5) 6-4 | H2H | 3 | 129 | 5 | 3 | 68.5% | 85.2% | 64.3% | 0/0 |
| 2019-08-26 | US Open | Hard | R128 | 33 | Denis Shapovalov | 19 | Felix Auger-Aliassime (18) | 6-1 6-1 6-4 | H2H | 5 | 98 | 3 | 8 | 54.8% | 85.0% | 54.5% | 5/5 |
| 2019-08-12 | Cincinnati Masters | Hard | R64 | 58 |  Miomir Kecmanovic (Q) | 21 | Felix Auger-Aliassime | 6-3 6-3 | H2H | 3 | 63 | 4 | 1 | 60.4% | 89.7% | 57.9% | 0/0 |
| 2019-08-05 | Canada Masters | Hard | R16 | 8 |  Karen Khachanov (6) | 21 | Felix Auger-Aliassime | 6-7(7) 7-5 6-3 | H2H | 3 | 170 | 11 | 3 | 59.4% | 71.4% | 48.8% | 7/12 |
| 2019-08-05 | Canada Masters | Hard | R64 | 21 | Felix Auger-Aliassime | 205 | Vasek Pospisil (WC) | 6-2 6-7(3) 7-6(3) | H2H | 3 | 153 | 9 | 7 | 68.8% | 82.8% | 51.7% | 0/1 |
