This retrospective case series looks at the rare cases of lacrimal drainage system malignancies. The authors have identified 14 patients in 24 years, at a tertiary referral centre in the Indian subcontinent. Many previous publications have found squamous cell carcinoma (SCC) to be the most common malignancy of the lacrimal sac, however this paper has found the most common amongst their cohort to be transition cell carcinoma (28.5%) followed by mucoepidermoid carcinoma (21.4%) and SCC (14.2%). They found the most common presenting complaint to be a mass in the medial canthal area (64.2%) followed by epiphora (35.7%). The textbook complaint of bloody tears was only present in two patients (14.2%). Fifty percent of patients were misdiagnosed as nasolacrimal duct obstruction and 42.8% had already undergone dacryocystorhinostomy (DCR). The preferred management of the authors is wide local excision with post-op radiotherapy for epithelial tumours and radiotherapy (with or without chemotherapy) for malignant lymphomas.