Hello, sorry to hear about Winnie. It can be associated with an infected tear duct, a foreign object (foxtail) in the vicinity of his eye or tear ducts, and much less likely a tooth root infection.
Winnie should be evaluated by a veterinarian. A sedated exam may be best to fully examine his oral cavity, tear ducts and eyes. Please monitor him for any pain, squinting, nasal discharge, or worsening ocular discharge and have him evaluated sooner if you note any of these.