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Introduction: Residual ovarian syndrome (ROS) is a recognized complication following hysterectomy with ovarian preservation, manifesting as chronic pelvic pain, asymptomatic pelvic masses, or dyspareunia. The incidence of ROS is 2-3% and almost 75% of patients with ROS require surgery within 10 years after hysterectomy. Aim: We aim to present a unique case of ROS complicated by a rare occurrence of small bowel obstruction, detailing clinical features, imaging findings and treatment strategies. Case Report: A 35-year-old woman presented to Shreeji hospital, Gujarat on 5th April 2024 with severe abdominal pain, nausea and vomiting from 1 week and constipation from the past 3 days. She was tachycardiac, rest vitals were normal. Her abdomen was distended with absent bowel sounds. She was tender in the left upper quadrant and a large pelvic mass was palpated. Contrast-enhanced CT scan of the abdomen demonstrated a 12.3 x 8.3 x 6 cm cystic lesion at right iliac fossa and dilatated jejunum with multiple air-fluid levels consistent with intestinal obstruction. She had an operative history of obstetric hysterectomy due to postpartum hemorrhage in caesarean section in 2016 during her third pregnancy, the ovaries left in situ. A diagnosis of ROS was made with intestinal obstruction. Result: Laparoscopic cystectomy and oophorectomy was done on 6th April 2024 after reduction of obstruction and extensive adhesiolysis. Post-operative recovery was uneventful with resolution of symptoms. Conclusion: ROS with small bowel obstruction is a rare clinical finding, hence emphasizing the need for vigilance in clinical evaluation and management becomes important. Surgical intervention remains the cornerstone for symptomatic relief and prevention of complications. While pharmacologic therapies (gonadotropin-releasing hormone analogs or high dose progesterones) may provide temporary relief, definitive treatment often necessitates surgical intervention. However, there are limited data supporting the efficacy of pharmacologic therapy.