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A case of squamous cell carcinoma (SCC) of the head and neck that developed thrombosis inside the flap during the surgery and subendocardial infarction after the surgery is presented. An 82-year-old man was referred to our hospital because of nonhealing of a tooth extraction socket. The patient's medical history was unremarkable, with no ischemic heart disease. The preoperative blood tests and the physiological and imaging findings were also unremarkable other than an elevated hemoglobin A1c (HbA1c; 6.6%). He was diagnosed with SCC of the lower gingiva on biopsy. After intensive insulin therapy for glycemic control, tumor resection including mandibular segmental resection and neck dissection, followed by reconstruction with a vascularized fibular flap, was performed. Although there was visible thrombosis inside the fibular veins of the flap during the surgery, microvascular anastomosis and reconstruction were done without any complications after irrigation with heparin saline. Subendocardial infarction developed 10 hours after the surgery in the intensive care unit, but circulatory dynamics recovered after percutaneous coronary intervention. Two years after the surgery, the patient has had no decrease in basic activities of daily living, no local tumor recurrence, and no distant metastasis.