Background and purpose: There is conflicting evidence with respect to the correlation between neoadjuvant chemoradiation and anastomotic complications following trimodality therapy in patients with esophageal cancer. We aimed to analyze the relationship between their dosimetry and any resulting anastomotic complications. Materials and methods: The medical records of 51 consecutive patients who underwent trimodality therapy between 2007 and 2014 were retrospectively reviewed. We analyzed the differences in the mean dose received by regions of the esophagus relative to the landmark of the azygous vein and the stomach to correlate the development of an anastomotic complication using nonparametric rank-sum tests. Results: Anastomotic leakage and stricture rates were 12% and 22%, respectively. Patients with anastomotic complications received a statistically significant higher mean dose to the esophagus at the level of the azygous vein (0.0 cm) and lower (up to −2.7 cm) (28.4–42.2 Gy vs. 10.3–27.6 Gy, p