Epidermoid cysts are benign lesions, characterized by cystic spaces lined by simple squamous epithelium (epidermoid cyst), containing skin adnexa (''true'' dermoid cyst) or tissues of all three germ layers (teratoid cyst). Head and neck constitute *7% of all cases of epidermoid and dermoid cysts. There is often a diagnostic dilemma with the more common cystic lesions of this region. A retrospective case-series study of histologically proved epidermoid cysts in the head-neck region, from February 2008 to January 2011, in the Department of Otorhinolaryngology and Head-Neck Surgery of a tertiary Government teaching hospital in eastern India. The diagnosis was reached by fine needle aspiration cytology FNAC and subsequent histopathology where feasible. Necessary imaging was done for evaluation and management. A total of 28 cases were analyzed. 5 were female, with a male: female ratio of 4.6. Age range was from 2 to 60 years (mean = 30). Excision was the preferred treatment in 20 cases (71.4%). Various sites like the submandibular region (5), pinna (5), sublingual region (1), periorbital (6), suprasternal (6), along the anterior border of sternocleidomastoid (1) and glabella (3) were involved, along with an iatrogenic implantation epidermoid cyst in a tracheostomy scar. Some of the interesting cases presenting with clinical dilemma have been emphasized. Epidermoid cysts are relatively less common in the head-neck region, hence are liable to be misdiagnosed. In this case-series, few cases presenting with enough elements of confusion and dilemma are discussed with overall analysis and review of the related literature.