Candida bezoar is a rare pathologic entity characterized by the colonization of a cavity by an aggregate or mass of mycelia due to local or systemic infections with Candida spp. Candida bezoar is commonly seen in immunocompromised individuals and can often present in the context of symptomatic urinary tract infection or urosepsis. The implicated risk factors for the development of Candida bezoars are anatomical urinary tract abnormalities, diabetes mellitus, indwelling urinary catheters, increased use of broad-spectrum antibiotics, and corticosteroids. Early clinical suspicion is essential for diagnosis to prevent the dissemination of disease and for a favorable prognosis. We report a case of a 49-year-old diabetic male who presents with hematuria, abnormal urinary flow, and left-sided flank pain for four days caused by a Candida bezoar of the urinary bladder resulting in unilateral obstructive uropathy despite the appropriate placement of a ureteral stent. Treatment with left nephrostomy tube, oral fluconazole, and amphotericin bladder irrigation for three days was successful. The patient's condition improved, and he was discharged on fluconazole and was recommended to follow up with urology as an outpatient.