Primary carcinomas of the lacrimal drainage system are rare. These malignant neoplasms typically present as noncompressible, nontender masses with low-grade dacyrocystitis and/or unilateral epiphora. Lymph node metastasis may occur late in the disease course. Complete surgical resection is the best treatment choice; extensive procedures such as orbital exenteration and maxillectomy may be necessary for complete tumor extirpation. Further adjunctive radiotherapy may improve local control. We present two cases of carcinoma of the lacrimal drainage system, including one locally controlled tumor with apparent lymph node metastasis that occurred 21 years after primary treatment. A review of the histopathology and literature concerning carcinomas of the lacrimal drainage system is presented.