First branchial cleft cysts are rare and can present as a diagnostic challenge to the physician. There can be frequent misdiagnoses, leading to a delay in treatment. This may result in mismanagement, causing an increased rate of recurrence. Moreover, their close relationship to the facial nerve would necessitate the exposure and preservation of the facial nerve. We report a case of a patient with the classical presentation of a Work type II branchial cleft cyst. Imaging showed a lesion just adjacent to the external auditory canal. Intraoperatively, a cartilage-lined blind-ending sac with hair-bearing contents duplicating the external auditory canal was found. The case highlights the need to consider the diagnosis of first branchial cleft anomaly especially in the presence of cysts and sinuses within the region of the parotid and the upper neck. Complete surgical excision would be the mainstay of treatment to prevent future recurrence.