| 2019-11-20 | Davis Cup Finals RR: ARG vs GER | Hard | RR | 35 |  Jan-Lennard Struff | 14 |  Diego Schwartzman | 6-3 7-6(8) | H2H | 3 | 109 | 1 | 3 | 77.1% | 64.8% | 50.0% | 3/5 |
| 2019-11-19 | Davis Cup Finals RR: ARG vs CHI | Hard | RR | 14 | Diego Schwartzman | 33 |  Cristian Garin | 6-2 6-2 | H2H | 3 | 73 | 1 | 2 | 64.3% | 47.2% | 35.0% | 4/10 |
| 2019-11-22 | Davis Cup Finals QF: ARG vs ESP | Hard | RR | 1 |  Rafael Nadal | 14 | Diego Schwartzman | 6-1 6-2 | H2H | 3 | 60 | 0 | 2 | 64.3% | 59.3% | 33.3% | 3/7 |
| 2019-10-28 | Paris Masters | Hard | R32 | 75 |  Kyle Edmund | 15 | Diego Schwartzman (14) | 7-5 6-3 | H2H | 3 | 77 | 6 | 1 | 68.9% | 85.7% | 47.4% | 0/0 |
| 2019-10-21 | Vienna | Hard | F | 5 |  Dominic Thiem (1) | 15 | Diego Schwartzman (5) | 3-6 6-4 6-3 | H2H | 3 | 145 | 9 | 1 | 62.2% | 76.5% | 41.9% | 3/6 |
| 2019-10-21 | Vienna | Hard | SF | 15 | Diego Schwartzman (5) | 14 |  Gael Monfils (4) | 6-3 6-2 | H2H | 3 | 74 | 0 | 0 | 74.1% | 75.0% | 64.3% | 4/4 |
| 2019-10-21 | Vienna | Hard | QF | 15 | Diego Schwartzman (5) | 9 |  Karen Khachanov (2) | 7-6(6) 6-2 | H2H | 3 | 102 | 2 | 1 | 61.1% | 65.9% | 57.1% | 1/3 |
| 2019-10-21 | Vienna | Hard | R16 | 15 | Diego Schwartzman (5) | 47 |  Sam Querrey | 6-7(5) 6-4 7-6(5) | H2H | 3 | 160 | 2 | 6 | 64.3% | 71.6% | 65.9% | 2/3 |
| 2019-10-21 | Vienna | Hard | R32 | 15 | Diego Schwartzman (5) | 66 | Pierre-Hugues Herbert | 6-4 6-4 | H2H | 3 | 106 | 2 | 0 | 67.6% | 71.7% | 54.5% | 4/5 |
| 2019-10-14 | Antwerp | Hard | R16 | 92 |  Marius Copil (Q) | 15 | Diego Schwartzman (3) | 6-4 5-7 7-6(7) | H2H | 3 | 161 | 13 | 4 | 57.1% | 76.6% | 45.8% | 4/8 |
