Background: We aim to analyze incidence and outcomes of patients hospitalized with hospital-acquired pneumonia (HAP) according to chronic obstructive pulmonary disease (COPD) status and sex in Spain (2016–2019). Methods: We conducted a retrospective cohort study using national hospital discharge data of patients ≥40 years with a primary diagnosis of HAP, using the specific diagnostics of non-ventilator (NV)-HAP and ventilator-associated pneumonia (VAP). Results: We identified 37,029 patients with HAP ((NV)-HAP 87.28%, VAP 12.72%), 13.40% with COPD. HAP incidence increased over time, but only in subjects without COPD (p < 0.001). In women, incidence of HAP and (NV)-HAP was similar regardless of COPD status, but VAP incidence was lower in COPD women (p = 0.007). In men, the incidence of (NV)-HAP was significantly higher in those with COPD, while VAP incidence was lower in COPD men (p < 0.001). The in-hospital mortality (IHM) was similar in men and women with and without COPD. The risk of dying in hospital increased with age, congestive heart failure, cancer, and dialysis among men and women with COPD. Men that underwent surgery had a lower risk of IHM. VAP increased 2.58-times the probability of dying in men and women. Finally, sex was not associated with IHM among COPD patients. Conclusions: Incidence of HAP was significantly higher in COPD patients than in those without COPD, at the expense of (NV)-HAP but not of VAP. When stratifying by sex, we found that the difference was caused by men. IHM was similar in COPD and non-COPD patients, with no significant change overtime. In addition, sex was not associated with IHM.