| 2021-11-27 | Davis Cup Finals RR: SRB vs GER | Hard | RR | 54 |  Dominik Koepfer | 42 |  Filip Krajinovic | 7-6(4) 6-4 | H2H | 3 | 119 | 2 | 4 | 55.4% | 63.4% | 57.6% | 5/8 |
| 2021-11-08 | Stockholm | Hard | R16 | 11 |  Felix Auger-Aliassime (2) | 42 | Filip Krajinovic | 6-3 6-4 | H2H | 3 | 91 | 8 | 3 | 63.9% | 82.1% | 45.5% | 4/5 |
| 2021-11-08 | Stockholm | Hard | R32 | 42 | Filip Krajinovic | 248 |  Denis Istomin (Q) | 6-4 6-2 | H2H | 3 | 63 | 4 | 1 | 54.3% | 88.0% | 71.4% | 0/0 |
| 2021-11-01 | Paris Masters | Hard | R64 | 25 |  Reilly Opelka | 42 | Filip Krajinovic | 6-3 7-6(4) | H2H | 3 | 79 | 19 | 2 | 55.0% | 84.8% | 77.8% | 0/0 |
| 2021-10-25 | Vienna | Hard | R32 | 4 | Alexander Zverev (2) | 40 | Filip Krajinovic | 6-2 7-5 | H2H | 3 | 81 | 12 | 3 | 61.0% | 80.6% | 52.2% | 5/6 |
| 2021-10-18 | Moscow | Hard | R16 | 61 |  Pedro Martinez | 37 | Filip Krajinovic (4) | 6-3 6-4 | H2H | 3 | 91 | 7 | 0 | 60.3% | 74.3% | 52.2% | 2/4 |
| 2021-10-04 | Indian Wells Masters | Hard | R32 | 2 |  Daniil Medvedev (1) | 34 | Filip Krajinovic (27) | 6-2 7-6(1) | H2H | 3 | 90 | 4 | 3 | 57.9% | 69.7% | 62.5% | 1/3 |
| 2021-10-04 | Indian Wells Masters | Hard | R64 | 34 | Filip Krajinovic (27) | 59 | Marcos Giron | 7-6(2) 7-5 | H2H | 3 | 106 | 1 | 5 | 64.9% | 76.0% | 51.9% | 6/8 |
| 2021-09-27 | Sofia | Hard | R16 | 37 | Filip Krajinovic (5) | 48 | Laslo Djere | 6-3 6-0 | H2H | 3 | 73 | 3 | 0 | 67.3% | 74.3% | 64.7% | 5/5 |
| 2021-09-27 | Sofia | Hard | R32 | 37 | Filip Krajinovic (5) | 462 |  Alexandar Lazarov (WC) | 6-0 6-3 | H2H | 3 | 65 | 4 | 1 | 64.1% | 80.0% | 64.3% | 1/1 |
