Introduction: Breast carcinoma commonly metastasizes to the lymph nodes, bones, lungs, liver, and brain, and synchronous metastatic involvement of both endometrial polyp and uterine leiomyomas are exceedingly rare occurrence. Case description: A 48-year-old female patient presented with a chief complaint of abnormal uterine bleeding and underwent total hysterectomy. Gross examination of the specimen showed a 6.0 cm pedunculated mass at the posterior endometrium with multiple well-defined, tan-white mass with whorl-like pattern, grossly consistent with endometrial polyp and leiomyomas, respectively. Microscopic sections of both the polyp and leiomyomas demonstrated tumor cells arranged in nests and solid sheets consisting of moderately pleomorphic tumor cells with irregularly round to oval, hyperchromatic to open vesicular chromatin, inconspicuous to visible nucleoli and abundant eosinophilic cytoplasm – features reminiscent of invasive carcinoma of the breast. Review of the patient’s past medical history revealed a diagnosis of breast cancer made three months prior to the onset of gynecologic symptoms. Discussion: Immunohistochemistry studies for Mammaglobin, GATA3 and PAX8 were performed which demonstrated positive staining for Mammaglobin and GATA3. PAX8 negativity excluded a primary gynecologic origin. In the context of the patient’s prior diagnosis of breast carcinoma, along with morphologic features and immunoprofile, this case was signed-out as metastatic breast carcinoma involving an endometrial polyp and uterine leiomyomas. Conclusion Endometrial polyp and uterine leiomyomas are two of the most common benign neoplasms in the gynecologic tract. Metastatic involvement of these lesions is exceedingly rare; to the best of our knowledge, there are only 15 reported cases of endometrial polyp and 24 leiomyoma metastases. Despite its rarity, both clinicians and pathologists alike must be aware of this entity to ensure accurate diagnosis and appropriate management.