| 2019-11-19 | Davis Cup Finals RR: USA vs CAN | Hard | RR | 15 |  Denis Shapovalov | 32 |  Taylor Fritz | 7-6(6) 6-3 | H2H | 3 | 87 | 2 | 1 | 57.8% | 70.3% | 55.6% | 2/4 |
| 2019-11-21 | Davis Cup Finals QF: AUS vs CAN | Hard | RR | 18 |  Alex de Minaur | 15 | Denis Shapovalov | 3-6 6-3 7-5 | H2H | 3 | 116 | 10 | 8 | 61.9% | 75.0% | 51.4% | 8/10 |
| 2019-11-24 | Davis Cup Finals F: CAN vs ESP | Hard | RR | 1 |  Rafael Nadal | 15 | Denis Shapovalov | 6-3 7-6(7) | H2H | 3 | 115 | 4 | 1 | 64.5% | 77.6% | 37.0% | 5/6 |
| 2019-11-23 | Davis Cup Finals SF: RUS vs CAN | Hard | RR | 15 | Denis Shapovalov | 17 |  Karen Khachanov | 6-4 4-6 6-4 | H2H | 3 | 110 | 5 | 2 | 69.4% | 71.2% | 53.8% | 2/5 |
| 2019-11-18 | Davis Cup Finals RR: ITA vs CAN | Hard | RR | 15 | Denis Shapovalov | 8 |  Matteo Berrettini | 7-6(5) 6-7(3) 7-6(5) | H2H | 3 | 172 | 15 | 2 | 65.3% | 75.9% | 66.7% | 7/7 |
| 2019-10-28 | Paris Masters | Hard | F | 1 |  Novak Djokovic (1) | 28 | Denis Shapovalov | 6-3 6-4 | H2H | 3 | 65 | 2 | 1 | 70.6% | 80.6% | 80.0% | 1/1 |
| 2019-10-28 | Paris Masters | Hard | QF | 28 | Denis Shapovalov | 13 |  Gael Monfils (13) | 6-2 6-2 | H2H | 3 | 59 | 5 | 0 | 64.1% | 92.0% | 64.3% | 0/0 |
| 2019-10-28 | Paris Masters | Hard | R16 | 28 | Denis Shapovalov | 6 |  Alexander Zverev (6) | 6-2 5-7 6-2 | H2H | 3 | 129 | 5 | 3 | 54.2% | 82.7% | 43.2% | 11/13 |
| 2019-10-28 | Paris Masters | Hard | R32 | 28 | Denis Shapovalov | 12 | Fabio Fognini (11) | 3-6 6-3 6-3 | H2H | 3 | 102 | 14 | 3 | 55.1% | 76.7% | 54.3% | 4/6 |
| 2019-10-28 | Paris Masters | Hard | R64 | 28 | Denis Shapovalov | 53 | Gilles Simon | 2-2 RET | H2H | 3 | 23 | 2 | 2 | 54.5% | 83.3% | 20.0% | 0/1 |
