We report two cases of lacrimal obstruction after ocular infection with monkeypox virus (MPX) in the 2022 outbreak. One of them was a distal canalicular obstruction and the other was a proximal canalicular obstruction. In the first days of MPX they presented with conjunctivitis and periocular skin vesicles. Several months after the ophthalmic condition was cured, they showed persistence of epiphora, and the lacrimal problem was diagnosed. The photographs taken during the inflammation of the anterior pole were reviewed and vesicles located in the same area as the canalicular damage were observed. One patient underwent a canaliculodacryorhinostomy and the other an exploratory punctoplasty. Both surgical operations failed to restore normal tear flow. Lacrimal drainage disorders related to ocular MPX have not yet been described. And, in addition, these cases are the first relation of viral vesicular skin lesions and canalicular obstructions.