Pilomatrixoma is a benign cutaneous adnexal tumor that differentiates toward hair follicle cells. It infrequently occurs in the periorbital region. In the periorbital area, it is often located in the upper eyelid and eyebrow region. Periorbital pilomatrixoma is often misdiagnosed clinically and is less common than other benign skin tumors. In this retrospective review, we evaluate the demographic, clinical, and histopathological data of patients with periorbital pilomatrixoma, treated from 2010 to 2023. A retrospective analysis of periorbital pilomatrixoma cases treated during a period of 13 years was performed. Deidentified data in relation to the age at surgical excision, gender, location, size, histopathological features, treatment, and recurrence were collected. All histological slides were reviewed by an attending histopathologist. A total of 77 cases of periorbital pilomatrixoma were diagnosed by histopathological examination and treated from 2010 to 2023. A slight female preponderance (56%) was noted, and the majority of cases (52%) were presented in the first 2 decades of life. The left periorbital region was involved in 45.5% of cases, and 54.5% in the right. The upper lid was the most affected site. Two cases of recurrence were reported. No malignant transformation was noted. Pilomatrixoma is an uncommon benign periorbital tumor, commonly misdiagnosed clinically. Ophthalmologists and surgeons should suspect pilomatrixoma in the periorbital region, especially in children or young adults. Complete surgical excision is curative, and recurrence is rare.