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First branchial cleft anomalies are rare congenital defects of the head and neck. This case report presents a 12-year-old patient with a draining cutaneous pit approximately 1-cm anterior and 5-mm inferior to the right angle of the mandible. Imaging revealed a fistula between the cutaneous pit and Eustachian tube. Further characterization with methylene blue injection into the cutaneous pit resulted in spillage through the right Eustachian tube. Surgical excision of the fistula revealed a cylindrical structure comprised of ectodermal and mesodermal features that most likely represented a Work Type 2 first branchial cleft fistula. Keywords: First branchial cleft, Branchial cleft fistula, Branchial cleft, Work Type 2, Eustachian tube