| 2019-10-21 | Basel | Hard | R32 | 64 |  Richard Gasquet | 52 |  Juan Ignacio Londero | 6-1 7-6(4) | H2H | 3 | 77 | 12 | 3 | 62.3% | 86.8% | 65.2% | 3/3 |
| 2019-10-14 | Moscow | Hard | R32 | 152 |  Lukas Rosol (Q) | 51 | Juan Ignacio Londero | 6-7(4) 7-6(7) 6-3 | H2H | 3 | 135 | 20 | 4 | 61.3% | 80.0% | 56.1% | 2/4 |
| 2019-10-07 | Shanghai Masters | Hard | R64 | 289 |  Andy Murray (WC) | 56 | Juan Ignacio Londero (Q) | 2-6 6-2 6-3 | H2H | 3 | 137 | 10 | 4 | 61.6% | 65.6% | 44.7% | 7/10 |
| 2019-09-30 | Tokyo | Hard | R32 | 56 |  Jordan Thompson | 59 | Juan Ignacio Londero | 6-3 3-6 6-3 | H2H | 3 | 117 | 10 | 1 | 62.1% | 75.9% | 51.5% | 9/11 |
| 2019-09-23 | Chengdu | Hard | R32 | 29 |  Dusan Lajovic (5) | 57 | Juan Ignacio Londero | 6-2 4-6 6-4 | H2H | 3 | 104 | 10 | 3 | 67.1% | 75.5% | 54.2% | 1/4 |
| 2019-08-26 | US Open | Hard | R64 | 1 | Novak Djokovic (1) | 56 | Juan Ignacio Londero | 6-4 7-6(3) 6-1 | H2H | 5 | 135 | 7 | 8 | 51.2% | 71.4% | 47.5% | 3/8 |
| 2019-08-26 | US Open | Hard | R128 | 56 | Juan Ignacio Londero | 46 |  Sam Querrey | 3-6 6-1 7-6(3) 7-5 | H2H | 5 | 144 | 10 | 9 | 57.9% | 83.3% | 54.2% | 2/5 |
| 2019-08-12 | Cincinnati Masters | Hard | R32 | 3 |  Roger Federer (3) | 55 | Juan Ignacio Londero (WC) | 6-3 6-4 | H2H | 3 | 61 | 9 | 0 | 66.0% | 77.1% | 83.3% | 1/1 |
| 2019-08-12 | Cincinnati Masters | Hard | R64 | 55 | Juan Ignacio Londero (WC) | 26 |  Matteo Berrettini | 7-6(3) 6-3 | H2H | 3 | 87 | 5 | 1 | 68.3% | 81.4% | 70.0% | 0/1 |
| 2019-07-29 | Los Cabos | Hard | R16 | 112 |  Soonwoo Kwon (Q) | 59 | Juan Ignacio Londero | 6-4 3-6 6-3 | H2H | 3 | 131 | 2 | 4 | 55.0% | 76.4% | 44.4% | 6/8 |
