PURPOSE: Anastomotic technique in minimally invasive esophagectomy (MIO) remains a critical determinant of postoperative outcomes. This study compares circular stapled end-to-side and linear stapled side-to-side intrathoracic anastomosis in MIO for oesophageal cancer, focusing on anastomotic leak rates, long-term stricture formation, as well as secondary outcomes including complications, recovery, and survival. METHODOLOGY: We conducted a retrospective cohort study of patients undergoing two-stage MIO with intrathoracic anastomosis for oesophageal cancer at a quaternary centre from January 2011 to December 2023. Exclusion criteria included age under 18, non-malignant pathology, or incomplete surgery. Patients were grouped by anastomotic technique (circular vs. linear stapled), demographic, clinical, and outcome data were analysed. RESULTS: Of 265 patients, 245 met inclusion criteria (161 circular, 84 linear). Baseline characteristics were comparable. The overall anastomotic leak rate was 11% higher in the circular group (13%) versus linear (7%), though more severe (grade 3) leaks were seen in the linear group. Stricture rates were similar between techniques (17.4% circular vs.16.6% linear). Median postoperative length of stay was 10 days in both groups and thirty-day readmission was slightly higher in the linear group (20% vs.17.4%), without statistical significance. Multivariate analysis identified active or recent smoking (within 3 months) as an independent predictor of stricture formation. CONCLUSION Both techniques resulted in similar stricture and recovery outcomes. Circular stapled anastomoses were associated with a higher overall leak rate, while linear stapled techniques had more severe leaks. Smoking status remains a significant modifiable risk factor for anastomotic stricture formation and should be addressed preoperatively.