Cavernous sinus thrombosis is a rare but fatal condition arising due to various infectious and noninfectious causes. Although its incidence is very low in the setting of head and neck surgery, including radical neck dissection, a high index of suspicion with prompt treatment is the key to a successful outcome. We report a case of a 50-year-old woman with a chondrosarcoma of left lower alveolobuccal complex who underwent en bloc tumour resection with infratemporal fossa clearance and left modified radical neck dissection. Subsequently, she developed cavernous sinus thrombosis, which was successfully managed with a multidisciplinary approach. This case highlights the importance of high clinical suspicion in the postoperative setting to diagnose this potentially lethal complication.