Purpose: The purpose of this case series is to understand the prevalence, clinical significance, pathophysiology, pathology findings, and workup of uterine lipoleiomyomas. Methods: This case series, with cases in February and March of 2023, includes the presentation, clinical management, and pathologic diagnosis of two separate uterine lipoleiomyomas. Separate chart reviews were performed on each patient, including frozen and permanent section pathologic findings. Micropictographs were obtained from hematoxylin and eosin-stained slides. This project was acknowledged as “IRB-exempt” by the MU Institutional Review board. Results: Case 1: A 51-year-old G3P2 woman presented with six months of severe postmenopausal bleeding, severe left-lower quadrant pelvic pain, and lightheadedness. A transvaginal ultrasound revealed a heterogeneous, thickened endometrial echo of 3.9 centimeters and a probable left ovarian dermoid cyst. CT showed distension of endometrial cavity due to polyps and/or submucosal masses, as well as a fat-containing mass in the uterine corpus. Hysteroscopy with dilation and curettage was performed with pathology of high-grade malignancy. Differential diagnosis at this time included high-grade stromal sarcoma, undifferentiated carcinoma, adenosarcoma, or malignant mixed Mullerian tumor. Patient underwent MRI due to concern for malignancy, which showed FDG-avid endometrial thickening with no other FDG-avid areas of concern. Histopathologic diagnosis found carcinosarcoma of the uterus, two positive lymph nodes, and an incidental finding of lipoleiomyoma. Plan for medical management with gynecologic oncology will include chemotherapy and vaginal cuff brachytherapy for uterine carcinosarcoma. Case 2: A 50-year-old G5P5 woman presented with increasing vaginal spotting and worsening urge incontinence. CT showed increased size of heterogeneous mass in right lateral uterine wall, consistent with previously identified fibroid/leiomyoma. An adjacent fat-containing lesion was identified within the uterine wall. Patient underwent MRI which revealed large uterine mass at the fundus, with an associated fatty component. Due to the abnormal rate of fibroid growth, and the fat component, there was concern for uterine sarcoma and/or malignant transformation of leiomyoma. Histopathologic diagnosis found lipoleiomyoma with benign atrophic endometrium, paratubal cysts of bilateral fallopian tubes, and follicular cyst of the right ovary. Follow-up in one year was recommended. Conclusion: Lipoleiomyomas are uncommon benign entities, occurring most commonly in postmenopausal women, similarly to uterine fibroids. While asymptomatic patients can be managed conservatively, these tumors can cause vaginal bleeding, pain, and urinary or fecal incontinence and can be definitively treated with hysterectomy. While imaging is necessary to initially characterize the lesion and determine concern for malignancy, histopathologic diagnosis remains the gold standard for diagnosis. Lipoleiomyomas are associated with other gynecologic malignancies, metabolic disorders, and rarely tumor-to-tumor metastasis. For this reason, careful clinical evaluation and surgical management are required for complete evaluation of the patient.