Background: Proliferating trichilemmal tumors are slow-growing lobulated masses most commonly found on the scalp of elderly women. Due to the locally invasive nature of the lesion, the treatment is complete excision of the tumor with tumor-free margins. Methods: We present two cases of trichilemmal tumors that exhibited aggressive local invasion across tissue planes. The first case had dural invasion, which needed dural reconstruction. The second case had muscle invasion, which required wide resection. Results: Sixteen months after their surgeries, the patients are in good health without any recurrence of tumors. Conclusion: Trichilemmal tumors may exhibit aggressive local invasion across tissue planes and even penetrate intracranially, causing considerable morbidity and mortality. The possibility of dural and muscle invasion must be kept in mind in order to achieve successful treatment results. A close clinical follow-up is judicious for detecting recurrences or metastases.