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Abstract Objectives Patients undergoing a prior failed attempt of chronic total occlusion‐percutaneous coronary intervention (CTO‐PCI) represent a challenging subgroup across all patients undergoing CTO‐PCI. There are limited data on the effects of a prior failed attempt on the outcomes of subsequent CTO‐PCI. We aimed to compare the procedural results and 24‐month outcomes of prior‐failed‐attempt CTO‐PCI with those of initial‐attempt CTO‐PCI. Methods Patients who underwent attempted CTO‐PCI between January 2017 and December 2019 were prospectively enrolled. We analyzed the procedural results and 24‐month major adverse cardiac events (MACE) between patients who underwent prior‐failed‐attempt and initial‐attempt CTO‐PCI. MACE was defined as a composite of cardiac death, target vessel‐related myocardial infarction, and ischemia‐driven target vessel revascularization (TVR) during follow‐up. Results In total, 484 patients who underwent CTO‐PCI (prior‐failed‐attempt, n = 49; initial‐attempt, n = 435) were enrolled during the study period. After propensity score matching (1:3), 147 patients were included in the initial‐attempt group. The proportion of the Japanese‐CTO (J‐CTO) score ≥2 was higher in the patients who underwent prior failed attempt than in those who underwent initial attempt (77.5% vs. 38.8%, p