| 2022-01-31 | Cordoba | Clay | QF | 139 |  Juan Ignacio Londero (WC) | 136 |  Nikola Milojevic (LL) | 6-4 7-5 | H2H | 3 | 95 | 7 | 1 | 59.7% | 85.0% | 37.0% | 2/4 |
| 2022-01-31 | Cordoba | Clay | R16 | 136 | Nikola Milojevic (LL) | 128 | Tomas Martin Etcheverry (WC) | 6-3 7-6(4) | H2H | 3 | 116 | 1 | 1 | 62.9% | 70.5% | 61.5% | 2/4 |
| 2022-01-17 | Australian Open | Hard | R128 | 55 |  Mackenzie McDonald | 139 | Nikola Milojevic (Q) | 5-7 6-4 6-3 6-2 | H2H | 5 | 155 | 7 | 3 | 57.8% | 79.4% | 54.3% | 3/7 |
| 2021-04-19 | Serbia | Clay | R16 | 33 | Filip Krajinovic (5) | 134 | Nikola Milojevic (WC) | 6-1 6-1 | H2H | 3 | 69 | 1 | 4 | 58.1% | 68.0% | 72.2% | 2/2 |
| 2021-04-19 | Serbia | Clay | R32 | 134 | Nikola Milojevic (WC) | 90 | Federico Coria | 6-4 6-0 | H2H | 3 | 80 | 5 | 4 | 52.5% | 67.7% | 57.1% | 3/4 |
| 2021-04-05 | Marbella | Clay | R32 | 133 |  Carlos Alcaraz (WC) | 129 | Nikola Milojevic (Q) | 7-6(3) 6-3 | H2H | 3 | 98 | 1 | 1 | 71.0% | 79.5% | 55.6% | 0/1 |
| 2020-09-28 | Roland Garros | Clay | R64 | 56 | SLOAljaz Bedene | 144 | Nikola Milojevic (Q) | 7-5 2-6 6-1 7-6(4) | H2H | 5 | 174 | 16 | 4 | 61.8% | 75.3% | 45.5% | 5/9 |
| 2020-09-28 | Roland Garros | Clay | R128 | 144 | Nikola Milojevic (Q) | 29 | Filip Krajinovic (26) | 6-4 3-6 6-3 6-1 | H2H | 5 | 190 | 1 | 7 | 57.5% | 65.6% | 53.3% | 7/11 |
| 2020-02-03 | Pune | Hard | R16 | 90 |  Egor Gerasimov (8) | 148 | Nikola Milojevic (Q) | 2-6 6-3 6-2 | H2H | 3 | 106 | 8 | 3 | 68.5% | 77.0% | 35.7% | 4/6 |
| 2020-02-03 | Pune | Hard | R32 | 148 | Nikola Milojevic (Q) | 126 |  Antoine Hoang | 7-6(5) 6-4 | H2H | 3 | 100 | 4 | 1 | 62.9% | 84.6% | 60.9% | 0/1 |
