Chyle leak is a well-recognized iatrogenic thoracic duct injury but a rare and serious complication of head and neck surgery affecting 1-2.5% of head and neck surgery dissections. It is potentially a life-threatening condition and management may be problematic and prolonged. Here we presented a rare case report of right sided chyle leak with its surgical management and review of literature. A 56-year-old patient with a complain of non-healing ulcer in the right buccal vestibule in the last 1-2 months reported to the outpatient department (OPD). After complete preoperative profile and counseling patient's consent was taken and wide local excision of lesion was done with bite composite resection with right hemimandibulectomy and maxillary alveolectomy till pterygoid plates, with right side selective neck dissection, level I-III followed by reconstruction with right side pectoralis major myofascial flap. Then the patient was on 5 days octreotide therapy. Regular post-operative follow-up was taken and no leak was noted further. In case of a chyle leak early diagnosis and aggressive treatment is essential to avoid local and systemic complications that prolong hospitalization.