The objective of the study was to highlight diagnostic dilemmas and suggest pointers toward early diagnosis of spontaneous rupture of urinary bladder based on case study of 2 patients diagnosed as a case of spontaneous rupture of urinary bladder. A 26-year-old man presented with painless progressive abdominal distension of 1-week duration. In absence of acute abdominal symptoms and signs, the diagnosis of chronic liver disease with ascites was entertained. Peritoneal fluid aspirate demonstrated high urea and creatinine levels. Computed tomographic (CT) scan of abdomen suggested urinary bladder rupture, which was further confirmed by CT cystogram. Another 34-year-old man presented with acute abdominal pain, hematuria, and features of peritonitis. There was no history of trauma. Foley catheterization revealed blood-stained urine. Ultrasonography abdomen suggested urinary bladder rupture, which was again confirmed by CT cystogram. Both patients made uneventful recovery after repair of bladder perforation. Spontaneous rupture of urinary bladder is extremely rare with only very few reports available in literature. High creatinine levels in the peritoneal fluid aspirate of the first patient and the blood-stained urine in the second patient were pointers toward possibility of urinary bladder rupture. Rupture of urinary bladder should always be considered in differential diagnosis of patients presenting with free fluid in abdomen/peritonitis, decreased urine output, hematuria and in whom increased level of urea/creatinine are detected in serum and/ or peitoneal fluid aspirate.