Objective: To report surgical and postoperative management of complicated total cystectomy in a dog with transitional cell carcinoma (TCC). Study design: Case report. Animals: One male neutered Shetland sheepdog.Methods: The dog was presented after a 1-month history of stranguria, unresponsive to oral antibiotic therapy. A craniodorsal bladder mass was identified by computed tomography (CT), and partial cystectomy was performed with 1-cm gross lateral margins (day 1). Results of histopathology provided evidence for a diagnosis of TCC, and the dog was treated with adjuvant mitoxantrone. The dog presented with uroperitoneum on day 67 after recurrence and spontaneous perforation. Total cystectomy and ureterourethral anastomosis were performed. Ureteral obstruction developed after removal of catheters that had been placed intraoperatively. Surgical revision included resection of the anastomosis site, bilateral ureteral stenting, and transection and reorientation of the distal urethra to facilitate tension-free closure. Postoperative leakage was managed with bilateral percutaneous nephrostomy tube placement. Results: The dog was discharged on day 88. Adjuvant treatment with vinblastine was pursued. Local recurrence was noted at day 154. Subcutaneous ureteral bypass was performed on day 247 to manage repeat obstruction. Repeated urinary tract infections were subsequently encountered. The dog was euthanized on day 368 because of abdominal discomfort and inappetence, with evidence of progressive urethral, ureteric, and abdominal wall TCC. Conclusion: Complicated cystectomy can be managed to provide survival comparable to previous reports regarding total cystectomy. Clinical significance: Nephrostomy tube placement, ureteral stenting, and subcutaneous ureteral bypass may be considered to manage complicated cystectomy.Preemptive stenting or urinary diversion may help prevent complications.