Background <p>Pulmonary metastases affect up to 30% of cancer patients, but the incidence depends on the primary tumor type. Advances in therapy have expanded indications for pulmonary metastasectomy beyond highly selected cases. This study investigated long-term outcomes and prognostic factors of repeated pulmonary metastasectomies in modern clinical practice.</p> Methods <p>This study analyzed the long-term results of 1503 pulmonary metastasectomies performed on 1106 consecutive patients at the Istituto Nazionale Tumori of Milan between 2003 and 2018, with a focus on multiple and repeated procedures, type of surgical resection, and key prognostic factors. Patients were stratified into three cohorts: single metastasis (SM, <i>n</i> = 530), multiple metastases (MM, <i>n</i> = 595), and recurrent metastases (RM, <i>n</i> = 378).</p> Results <p>The 10&#xa0;year survival rates were 35.5% overall, 41.1% for SM, 30.8% for MM, and 31.1% for RM. The median survivals were as 5.1, 5.4, 3.8, and 5.9&#xa0;years respectively. Precision resection was the most common type of procedure (53.2%), with 54.0% survival at 5&#xa0;years and 33.4% survival at 10&#xa0;years. The 30&#xa0;day postoperative mortality was 0.1% overall, 0% for SM, 0.3% for MM, and 0% for RM.</p> Conclusions <p>These findings highlight the feasibility and curative potential of multiple and repeated pulmonary metastasectomies for carefully selected patients.</p>