Inverted papilloma is a benign epithelial tumor of the nasal cavity. It is known to coexist with malignancy in 5 to 13% of cases, with squamous cell carcinoma being the most common malignancy. Another associated malignancy, one that is extremely rare, is verrucous carcinoma. To the best of our knowledge, no case of verrucous carcinoma occurring alone or in association with another neoplasm has been described in the nasolacrimal system. We report a case of synchronous verrucous carcinoma and inverted papilloma of the lacrimal sac in a 47-year-old man. The patient presented with epiphora, nasal obstruction, swelling of the left medial canthus, and drainage of a foul-smelling fluid from the left nostril. Computed tomography and magnetic resonance imaging detected the presence of a large mass occupying the left nasal cavity and sinuses with extension into the nasopharynx. In addition, bony invasion of the anteroinferomedial wall of the left orbit was noted with extension of the tumor into the orbit itself, which resulted in lateral displacement of the left medial rectus muscle. The patient underwent endoscopic debulking of the left sinonasal lesion. Of note, the surgery had to be completed in stages because of excessive blood loss. Histopathologic examination of the intranasal component of the tumor identified it as an inverted papilloma. One month after the intranasal resection, a left dacryocystectomy was performed; histopathologic examination revealed that an invasive verrucous squamous cell carcinoma had arisen within the inverted papilloma.