(1) Background: It is not well known whether there is an association between COPD and hemorrhagic stroke (HS). We aim to analyze the incidence, clinical characteristics, procedures, and outcomes of HS in patients with and without COPD and to assess sex differences. Secondly, to identify factors associated with in-hospital mortality (IHM). (2) Methods: Patients aged ≥40 years hospitalized with HS included in the Spanish National Hospital Discharge Database (2016–2018) were analyzed. Propensity score matching (PSM) was used to compare patients according to sex and COPD status. (3) Results: We included 55,615 patients (44.29% women). Among men with COPD the HS adjusted incidence was higher (IRR 1.31; 95% CI 1.24–1.57) than among non-COPD men. COPD men had higher adjusted incidence of HS than COPD women (IRR 1.87; 95% CI 1.85–1.89). After matching, COPD men had a higher IHM (29.96% vs. 27.46%; p = 0.032) than non-COPD men. Decompressive craniectomy was more frequently conducted among COPD men than COPD women (6.74% vs. 4.54%; p = 0.014). IHM increased with age and atrial fibrillation, while decompressive craniectomy reduced IHM. (4) Conclusions: COPD men had higher incidence and IHM of HS than men without COPD. COPD men had higher incidence of HS than COPD women. Decompressive craniectomy was more frequently conducted in COPD men than COPD women and this procedure was associated to better survival.