Background/Objectives: Surgical pulmonary resection in lung cancer remains the cornerstone of curative treatment; however, it is associated with considerable postoperative pulmonary complications. Patients previously treated for head and neck cancer (HNC) have a significantly increased risk of developing second primary lung cancer (LC) and a higher incidence of adverse pulmonary outcomes after LC resective surgery due to increased baseline frailty. Methods: A retrospective observational longitudinal study was conducted on 1679 patients who underwent surgical resection with curative intent for LC at the Thoracic Surgery Department of Hospital Clínico San Carlos, Madrid, Spain, between December 1989 and December 2024. Patients were divided into two groups based on the presence or absence of prior HNC: 87 with HNC vs. 1592 without. Special attention was paid to respiratory complications, particularly bronchopleural fistula (BPF), empyema, atelectasis, and pneumonia. Variables significantly associated with BPF and HNC in univariate analyses (excluding those related to other complications to avoid collinearity), as well as clinically relevant baseline differences between groups, were included in a stepwise multivariable logistic regression modeling procedure to identify independent risk factors associated with BPF. Results: In comparison with the control group, significantly higher rates of postoperative BPF (12.6% vs. 3.6%), empyema (10.3% vs. 2.8%), atelectasis (14.9% vs. 8.3%) and need of reintervention (10.3% vs. 4.2%) were found in the HNC group under unadjusted approach and stratified by surgery period. Sex, history of HNC, chronic obstructive pulmonary disease (COPD) and length of preoperative hospital stay were independently associated with BPF according to several multivariable logistic regression fits, which showed a moderate discriminatory capacity (AUC values ranging from 0.723 to 0.732). In particular, the presence of HNC was significantly associated with BPF, with adjusted odds ratio (aOR) estimates ranging from 3.562 (95% CI: 1.773 to 7.156) to 3.789 (95% CI: 1.863 to 7.709). Conclusions: In our study, COPD, male sex, preoperative hospital stay as well as HNC history were found independently associated with an increased odds of BPF after surgical treatment for LC. In particular, patients previously treated for HNC had more than threefold higher odds of developing BPF than those without a history of HNC, with this association remaining consistent over the 35-year study period.