Acquired ano-rectal fistulas and sinuses are frequently observed clinical conditions, with a higher prevalence in men. While these conditions typically remain confined to the ano-rectal region, the potential for involvement of nearby pelvic genito-urinary structures exists due to their anatomical closeness. Interestingly, such cases are rarely documented in medical literature. This could be attributed to the protective role of anatomical barriers, such as pelvic fasciae, which limit the spread of inflammatory or infectious processes from the ano-rectal area to adjacent structures. In this article, we describe a series of four patients who presented with ano-rectal fistulas and sinuses that extended into pelvic genito-urinary organs. Among them, three were diagnosed with underlying inflammatory bowel disease. The unusual symptoms observed in all cases posed diagnostic challenges, necessitating a thorough evaluation. This series highlights the importance of considering atypical presentations in patients with complex ano-rectal pathologies and underscores the value of multidisciplinary approaches in achieving accurate diagnoses and effective treatment plans.