Ovarian neoplasms are categorized based on histopathologic features into epithelial surface cell tumors, germ cell tumors (teratomas), sex cord-stromal tumors, and metastases. Teratomas are the most common ovarian germ cell neoplasms. They are generally slow-growing lesions and can get fairly large before becoming symptomatic. The lesions are often incidentally discovered during imaging for other diagnostic purposes. Complications are uncommon but occur more commonly with larger lesions and include torsion, malignant degeneration, rupture, and rarely infection. When sizable, ovarian dermoid can rarely rupture and result in spillage of proteinaceous content into the peritoneal cavity, which can lead to chemical peritonitis. Additionally, the lesion can fragment into smaller lesions and can get implanted at different sites within the abdomen and pelvis. We present a case with an atypical presentation of a ruptured dermoid in a patient presenting with right upper quadrant pain who underwent sonographic evaluation, which demonstrated acute calculus cholecystitis but incidentally was found to have a partially calcified right subphrenic mass. Subsequent evaluation with computed tomography (CT) demonstrated multiple scattered peritoneal and mesenteric masses containing fat and calcification, highly suggestive of a chronically ruptured dermoid cyst.