First branchial cleft anomalies are quite rare, and the majority of them are found in and around the ear canal, mostly superficial to the facial nerve. Very rarely, the anomalous tract of the first branchial cleft can go deeper to the facial nerve, necessitating a meticulous and extensive surgery. A 21-year-old student presented with slowly increasing cystic swelling in the infra-auricular region. Findings of the magnetic resonance imaging were consistent with the first branchial cleft cyst, which also exhibited a deeper extent of the lesion into the parapharyngeal space. The entire tract was excised along with the superficial parotidectomy by an open approach. In addition to illustrating the presentation and management of this peculiar case, the present report also reviews the latest literature around their management.