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Simple Summary: For centrally located non-small cell lung cancer (NSCLC), sleeve lobectomy would be preferable to pneumonectomy (PN). In this context, however, the role of complex sleeve lobectomy (CLS) is still poorly understood. Our study compared CLS with PN using a retrospective analysis. Research shows that CLS has a lower 90-day mortality rate and fewer major complications compared to PN, while oncological outcomes remain comparable. These results support the contention that CLS is a safe and effective procedure for centrally located NSCLC, even after neoadjuvant treatment. Background: Standard sleeve lobectomies are recommended over pneumonectomy (PN), but the efficacy and oncological proficiency of complex sleeve lobectomies (CSLs) have not been completely investigated. The aim of this study was to report our experience in CSL in patients affected by a centrally located non-small-cell lung cancer (NSCLC), comparing all the variables and outcomes with PN. Methods: From 2014 to 2022, we collected the data of patients who underwent PN and CSL for NSCLC, excluding neuroendocrine tumors, salvage surgery or carinal resection. Regression analysis was used to assess the association between procedures and complications; the Kaplan–Meier method and Cox regression analysis were used to evaluate survival and risk factors of reduced survival. Results: We analyzed n = 38 extended sleeve lobectomies and n= 6 double-sleeve lobectomies (CSL group) and n= 60 PNs. We had a trend toward higher postoperative mortality in the PN group (5% vs. 0%, p = 0.13). Major complications and bronchial fistula developed in 21.7% and 6.8% (p = 0.038) and in 6.7% and 4.5% (p = 0.64), respectively. The right side was identified as risk factor for major complications, whereas age > 70 and PN had a trend of association in multivariable analysis. The median OS was similar between the two groups (p = 0.76) and cancer recurrence was the only significant risk factors of reduced OS. Excluding functionally compromised patients, the OS of CSL was better than that of PN (67% vs. 42%, p = 0.25). Conclusions: Considering that major complications are often associated with mortality after surgery for centrally located NSCLC, CSLs could be considered an alternative to PN while also ensuring comparable survival. [ABSTRACT FROM AUTHOR]