(1) Background: To examine trends in incidence and outcomes of urinary tract infections (UTIs) among men and women with or without chronic obstructive pulmonary disease (COPD), and to identify the predictors for in-hospital mortality (IHM). (2) Methods: We included patients (aged ≥40 years) who were hospitalized with UTIs between 2001 and 2018. Data were collected from the Spanish National Hospital Discharge Database. (3) Results: We identified 748,458 UTI hospitalizations, 6.53% with COPD. The UTIs incidence increased over time. It was 1.55 times higher among men COPD patients than among non-COPD men (incidence rate ratio (IRR) 1.55; 95% CI 1.53–1.56). The opposite happened in women with COPD compared to non-COPD women (IRR 0.30; 95% CI 0.28–0.32). IHM was higher in men with COPD than non-COPD men (5.58% vs. 4.47%; p < 0.001) and the same happened in women (5.62% vs. 4.92%; p < 0.001). The risk of dying increased with age and comorbidity, but the urinary catheter was a protective factor among men (OR 0.75; 95% CI 0.64–0.89). Multivariable analysis showed a significant reduction in the IHM over time for men and women with COPD. Suffering from COPD only increased the risk of IHM among men (OR 1.07; 95% CI 1.01–1.13). (4) Conclusions: The incidence of UTIs increased over time. Suffering COPD increased the risk of IHM among men, but not among women.