Acute dacryocystitis and orbital cellulitis are conditions with serious implications, particularly among pediatric patients. The co-occurrence of these conditions in children is rare, and their association with coronavirus disease 2019 (COVID-19) infection introduces a unique dimension. We present the case of a five-year-old boy who presented to the pediatric emergency department with left periorbital swelling, erythema, and excessive tearing. He had a history of low-grade fever and rhinorrhea, raising concerns about COVID-19. Upon physical examination, we observed significant periorbital swelling and erythema, accompanied by conjunctival injection and chemosis. The diagnosis encompassed acute dacryocystitis and cellulitis, with subsequent confirmation of COVID-19 through testing. Imaging confirmed the presence of post-septal cellulitis and ethmoid sinus opacification. The patient received intravenous antibiotics, leading to clinical improvement and eventual discharge for outpatient follow-up. This case underscores the importance of maintaining a high index of suspicion for unusual presentations in pediatric patients. Successful management involved a multidisciplinary approach, emphasizing the significance of promptly initiating antibiotic therapy and adopting conservative measures for nasolacrimal duct obstruction.