Background: Recto-sigmoid and rectal tumors are now treated with anterior resection as the gold standard. However, anastomotic leakage and the temporary use of a covering stoma after resection provide a significant problem for colorectal surgeons. The technique of anastomosis is critical in preventing anastomotic leakage. Some surgeons believe that side-to-end anastomosis is superior to end-to-end anastomosis, whereas others do not. Objective: The current study was aimed to compare the surgical outcome, particularly the incidence of anastomosis leakage, between two groups using various surgical techniques. Patients and Methods: This is a prospective randomized clinical trial (RCT) that included 107 patients with recto-sigmoid and rectal malignancies. Between March 2018 and March 2022, patients were treated at Ain-Shams University Hospitals with elective laparoscopic anterior resection. Patients were divided into two groups using sealed envelope method. Following anterior resection, Group A had side-to-end anastomosis (SEA) using a double stapling technique, while Group B had end-to-end anastomosis (EEA) utilizing a trans-anal circular stapler. Results: After anterior resection, Group A (35 men and 20 women) received side-to-end anastomosis, while Group B (31 men and 21 women) underwent end-to-end anastomosis. There were no statistically significant differences between the two groups as regard body mass index (BMI), smoking and tumor location. The end-to-end anastomosis group had a statistically significantly longer mean operative time than the side-to-end anastomosis group (251.71 vs. 227.15 minutes, respectively) (P value 0.001). There was no statistically significant difference in anastomotic leakage between the two groups, with a P value of 0.262 (2 instances, 3.6% in SEA Group vs. 5 cases, 9.6% in EEA Group). Conclusion: It could be concluded that side to end colorectal anastomosis could be an alternative to end to end with shorter operative time.