Summary Managing esophageal squamous cell carcinoma (ESCC) in patients with a history of cervical radiotherapy for a head and neck cancer (HNC) often requires a careful evaluation of esophagectomy due to concerns regarding complications and prognosis. This study evaluates the periesophagectomy and oncological outcomes of such patients. Patients diagnosed with ESCC between January 2010 and August 2023 and who had undergone esophagectomy with cervical anastomosis were retrospectively reviewed. Patients were categorized into two groups based on the presence (group 1) or absence (group 2) of a history of radiotherapy for as HNC. After 1: 2 propensity score matching, the perioperative and oncological outcomes, including overall survival (OS) and recurrence-free survival (RFS), were evaluated. A total of 481 patients, 32 in group 1 and 449 in group 2, were included. After matching, group 1 patients and 64 patients in the group 2 were analyzed. All the patients in group 1 were males, and their mean age was 56 years. The median radiation dose was 69 Gy. The rates of anastomosis leakage, pneumonia, respiratory failure, and reoperation were comparable between the two groups. However, vocal cord palsy occurred more frequently in group 1, particularly in those with recurrent laryngeal nerve lymph node dissection (37.5%). The 3-year OS (69.6% vs. 75.2%; p = 0.26) and RFS (50.8% vs. 55.9%; p = 0.63) were similar between groups 1 and 2. In conclusion, perioperative and oncological outcomes were comparable between ESCC patients with and without prior HNC radiotherapy, supporting esophagectomy as a feasible option.