| 2021-11-27 | Davis Cup Finals RR: ITA vs COL | Hard | RR | 10 |  Jannik Sinner | 111 |  Daniel Elahi Galan | 7-5 6-0 | H2H | 3 | 78 | 1 | 0 | 49.0% | 72.0% | 57.7% | 0/2 |
| 2021-11-29 | Davis Cup Finals QF: ITA vs CRO | Hard | RR | 10 | Jannik Sinner | 30 |  Marin Cilic | 3-6 7-6(4) 6-3 | H2H | 3 | 161 | 3 | 2 | 62.6% | 68.4% | 52.9% | 4/8 |
| 2021-11-26 | Davis Cup Finals RR: USA vs ITA | Hard | RR | 10 | Jannik Sinner | 24 |  John Isner | 6-2 6-0 | H2H | 3 | 62 | 1 | 2 | 70.6% | 87.5% | 80.0% | 3/3 |
| 2021-11-15 | Tour Finals | Hard | RR | 11 | Jannik Sinner (9) | 9 |  Hubert Hurkacz (7) | 6-2 6-2 | H2H | 3 | 85 | 5 | 0 | 56.5% | 74.4% | 50.0% | 5/5 |
| 2021-11-15 | Tour Finals | Hard | RR | 2 |  Daniil Medvedev (2) | 11 | Jannik Sinner (9) | 6-0 6-7(5) 7-6(8) | H2H | 3 | 149 | 18 | 5 | 70.6% | 76.4% | 60.0% | 3/5 |
| 2021-11-08 | Stockholm | Hard | R16 | 143 |  Andy Murray (WC) | 10 | Jannik Sinner (1) | 7-6(4) 6-3 | H2H | 3 | 135 | 8 | 2 | 49.2% | 71.9% | 69.7% | 1/1 |
| 2021-11-01 | Paris Masters | Hard | R32 | 35 |  Carlos Alcaraz | 9 | Jannik Sinner (8) | 7-6(1) 7-5 | H2H | 3 | 127 | 3 | 4 | 57.0% | 80.0% | 55.9% | 1/2 |
| 2021-10-25 | Vienna | Hard | QF | 11 | Jannik Sinner (7) | 8 |  Casper Ruud (4) | 7-5 6-1 | H2H | 3 | 97 | 10 | 0 | 67.7% | 76.2% | 40.0% | 4/5 |
| 2021-10-25 | Vienna | Hard | R16 | 11 | Jannik Sinner (7) | 116 |  Dennis Novak (WC) | 6-4 6-2 | H2H | 3 | 76 | 2 | 3 | 62.7% | 75.7% | 54.5% | 6/6 |
| 2021-10-25 | Vienna | Hard | R32 | 11 | Jannik Sinner (7) | 27 | Reilly Opelka | 6-4 6-2 | H2H | 3 | 63 | 1 | 1 | 69.0% | 93.1% | 69.2% | 0/0 |
