Leiomyomas, originating from smooth muscle cells, are common in the uterus but rare in the scrotum, presenting a clinical challenge. Scrotal leiomyomas, first described in the 19th century, are characterized by benign pathology from the subcutaneous dartos muscle. We present two cases of middle-aged males with scrotal leiomyomas, detailing clinical presentations, histopathological findings, and immunohistochemistry results. The first involved a 48-year-old with a painless scrotal lump, excised to reveal well-circumscribed smooth muscle bundles. Immunohistochemistry confirmed vimentin, desmin, and smooth muscle actin (SMA) positivity, consistent with scrotal leiomyoma. The second case featured a 25-year-old with a painless scrotal swelling, histologically matching the features of scrotal leiomyoma. Accurate diagnosis is crucial for guiding appropriate management strategies. Clinicians often employ a combination of clinical evaluation, imaging studies, and histopathological examination to confirm the presence of scrotal leiomyomas. Ultrasound remains a valuable tool for assessing the size, location, and vascularity of the tumor, aiding in the formulation of a differential diagnosis. Definitive diagnosis, however, relies on histological examination, which typically reveals spindle-shaped smooth muscle cells arranged in interlacing bundles.