The association between recurrent thyroglossal duct cyst (TGDC) and obstructive lingual tonsil hypertrophy has not previously been discussed. We present the case of a 7-year-old child whose medical and surgical course was complicated by these synchronous factors. The aim of this report is to present the risk factors for recurrence of TGDC and the unique challenge that concurrent lingual tonsil hypertrophy and airway obstruction present to management of patients.