Esophageal cancer is aprevalent cancer, with a high incidence in low socioeconomic category countries. Minimally invasive esophagectomy is increasingly being used to treat this malignant condition. However, anastomotic stricture is a serious complication post esophagectomy. The study aims to enhance diagnostic consistency, improve treatment methods, guide patient management, stratify outcomes, and offer evidence-based preventive interventions. A retrospective analysis of 550 patients who had minimally invasive esophagus surgery was carried out at Shaukat Khanum Memorial Cancer Hospital and Research Centre in Lahore between 2015 and 2020. All patients were treated with radical resection. For tumors of the lower esophagus and gastroesophageal junction, transhiatal esophagectomy was used; for tumors of the middle and upper thoracic esophagus, right video-assisted thoracoscopic surgery (VATS) was used in a three-stage procedure. Patients were routinely followed up two weeks after discharge, then every three, six, and 12 months. The mean age and BMI were 46.7 years and 19.4 kg/m2, respectively. Anastomotic leaks were rare, with only 13 patients experiencing them. The grade of tumor differentiation was poor, moderate, and well-differentiated. The study found that older age, high Eastern Cooperative Oncology Group (ECOG) performance status, and malignancies located in the upper and middle one-third of the esophagus had significant associations with anastomotic stricture. However, some variables, like sex, did not show significant associations in either analysis. The study reveals that factors such as older patient age, high ECOG performance status, single comorbidity, and malignancies located in the upper and middle one-third of the esophagus significantly influence anastomotic stricture. The study suggests that measures against anastomotic stricture such as endoscopic procedures and minimally invasive esophagectomy should be implemented to minimize the complications.