Intravascular Papillary Endothelial Hyperplasia (IPEH) is a rare benign vascular lesion of the skin and subcutaneous tissues that results from the proliferation of endothelial cells within a blood vessel. In this article, we present the case of an IPEH mimicking a Sister Mary Joseph Nodule on the umbilicus of a 53-year old female patient with ovarian cancer. A diagnostic workup was performed with a computerized tomography of abdominal cavity and pelvis showing an expansive cystic tumor formation with probable ovarian origin. Two separate histopathologic readings were done on the cutaneous lesion which revealed contradicting findings of benign versus malignant tumors. Immunohistochemical stains done showed that the lesion was positive for ERG and negative for epithelial differentiation markers. No surgical intervention was done at the time of consultation as a cutaneous metastasis was primarily considered initially. It is crucial to rule out a diagnosis of Sister Mary Joseph nodule, especially in a background of ovarian carcinoma as it may mimic vascular lesions occurring on the umbilicus. Immunohistochemical staining is a significant tool to precisely diagnose such lesions so that it is neither inadequately nor aggressively managed.