The objective of this study was to analyse the characteristics of healthcare-associated febrile urinary tract infection (HCA-FUTI) compared to community-acquired FUTI (CA-FUTI) in men. An ambispective cross-sectional study in which we recorded clinical and microbiology data and outcomes from males with FUTI attended in the Emergency Department was carried out. A total of 479 males with FUTI, 162 (33.8%) HCA-FUTI and 317 (66.2%) CA-FUTI, were included. HCA-FUTI patients were older (p < 0.001), had higher Charlson scores (p < 0.001) and received previous antimicrobial treatment more frequently (p < 0.001) compared to CA-FUTI patients. HCA-FUTI was less likely caused by Escherichia coli (p < 0.001) and more frequently by Klebsiella spp. (p = 0.02), Enterobacter spp. (p < 0.001) and Pseudomonas aeruginosa (p < 0.001). Resistance to ceftriaxone (p = 0.006), gentamicin (p < 0.001), quinolones (p < 0.001), co-trimoxazole (p = 0.001) and fosfomycin (p = 0.009) was higher among E. coli strains isolated from males with HCA-FUTI and so was the prevalence of extended-spectrum beta-lactamase and AmpC E. coli and Klebsiella spp.-producing strains (p = 0.012). Inadequate antimicrobial treatment and all-cause in-hospital mortality was associated with HCA-FUTI (p < 0.001 and p = 0.004, respectively). Independent factors for mortality were severe sepsis or septic shock [odds ratio (OR) 29; 95% confidence interval (CI): 3.9-214] and cirrhosis (OR 23.7; 95% CI: 1.6-350.6). Male patients with HCA-FUTI have different clinical characteristics, outcomes and microbiological features compared to CA-FUTI patients. Previous contact with the healthcare system has to be taken into consideration when deciding the optimal antimicrobial treatment in males with FUTI.