| 2019-04-08 | Marrakech | Clay | R16 | 75 |  Taro Daniel | 139 |  Adrian Menendez-Maceiras (Q) | 6-2 1-6 6-1 | H2H | 3 | 104 | 5 | 1 | 72.1% | 63.6% | 64.7% | 1/4 |
| 2019-04-08 | Marrakech | Clay | R32 | 139 | Adrian Menendez-Maceiras (Q) | 38 | Fernando Verdasco (6) | 5-7 6-2 6-2 | H2H | 3 | 151 | 7 | 5 | 54.6% | 79.2% | 45.5% | 3/5 |
| 2019-02-11 | New York Open | Hard | R32 | 166 |  Christopher Eubanks (Q) | 121 | Adrian Menendez-Maceiras (Q) | 6-4 7-6(4) | H2H | 3 | 88 | 14 | 1 | 73.1% | 71.4% | 61.1% | 5/5 |
| 2019-02-04 | Montpellier | Hard | R32 | 35 |  Jeremy Chardy (6) | 124 | Adrian Menendez-Maceiras (LL) | 6-1 6-1 | H2H | 3 | 46 | 9 | 1 | 65.7% | 87.0% | 75.0% | 0/0 |
| 2018-09-17 | St. Petersburg | Hard | R32 | 34 |  Denis Shapovalov (7) | 126 | Adrian Menendez-Maceiras (Q) | 7-6(3) 6-2 | H2H | 3 | 83 | 10 | 6 | 56.9% | 93.9% | 52.0% | 0/0 |
| 2018-07-23 | Gstaad | Clay | R32 | 89 | Jaume Munar | 149 | Adrian Menendez-Maceiras (Q) | 6-1 6-0 | H2H | 3 | 67 | 5 | 0 | 65.8% | 76.0% | 76.9% | 1/1 |
| 2018-02-12 | New York | Hard | QF | 25 | Adrian Mannarino (4) | 128 | Adrian Menendez-Maceiras (Q) | 7-5 2-6 6-3 | H2H | 3 | 150 | 10 | 1 | 68.6% | 61.1% | 51.5% | 6/10 |
| 2018-02-12 | New York | Hard | R16 | 128 | Adrian Menendez-Maceiras (Q) | 95 | Jeremy Chardy | 7-5 7-6(5) | H2H | 3 | 108 | 9 | 1 | 63.3% | 68.0% | 58.6% | 6/8 |
| 2018-02-12 | New York | Hard | R32 | 128 | Adrian Menendez-Maceiras (Q) | 49 | Steve Johnson (7) | 1-6 6-3 7-6(7) | H2H | 3 | 132 | 6 | 2 | 76.8% | 63.2% | 60.9% | 6/9 |
| 2018-02-05 | Quito | Clay | R32 | 152 | Corentin Moutet (WC) | 131 | Adrian Menendez-Maceiras | 6-4 6-7(5) 6-2 | H2H | 3 | 156 | 9 | 5 | 52.3% | 78.3% | 52.4% | 2/4 |
