Purpose Epiphora refers to the overflow of tears and most commonly results from insufficient drainage through the lacrimal excretory system. Nasolacrimal duct obstruction may have different aetiologies. Here we present a rare case of epiphora secondary to high grade lymphoma obstructing the nasolacrimal apparatus. Methodology A 63-year-old female presented to the ENT clinic with a 2-year history of right sided facial symptoms. Her main complaint was right sided epiphora and more recently right sided maxillary dental paraesthesia. She had also noticed right nasal obstruction as well as more noticeable cheek swelling. Apart from previous breast cancer surgery along with radiotherapy, she was otherwise well. Results On examination she had a right cheek mass palpable both through the skin of the cheek and through the sublabial gum. FNE showed a mass protruding through the inferior meatus in the nasolacrimal duct area. CT scan confirmed a right sided mass encompassing the right cheek, premaxillary area involving parts of the maxillary sinus and extending towards the nasolacrimal duct. MRI scan also showed a similar soft tissue mass in this area. Fine needle aspiration and core biopsy of the lesion was consistent with high-grade (large cell) lymphoma. Due to insufficient tissue for subtyping, a biopsy of the lesion was performed through a sublabial approach in the operating theatres. She was referred to the Haematology team for further treatment. Conclusion Chronic epiphora is a very rare symptom of lymphoma involving the head and neck region. It is prudent to perform a complete head and neck examination to prevent a misdiagnosis of dacrocystitis or dacryostenosis.