Introduction: Colorectal cancer (CRC) is the third most common malignancy and a major cause of cancer-related mortality worldwide. The optimal anastomosis technique after surgical resection remains controversial, as each method presents distinct advantages and drawbacks. In particular, antiperistaltic and isoperistaltic side-to-side anastomosis (SSA) are associated with varying benefits and postoperative outcomes. This study highlights the benefits of isoperistaltic SSA and compares its outcomes with existing literature on antiperistaltic techniques. Methods: A retrospective cohort study was conducted at King Hamad University Hospital, Bahrain, from February 2019 to September 2023, involving 24 patients undergoing laparoscopic or open right hemicolectomy with isoperistaltic SSA. Data collected included demographics, operative characteristics, and postoperative outcomes. Results: The cohort had a mean age of 56.17 years with 58.3% of the cohort being male. The average operative time was 207.5 minutes, with minimal blood loss and low transfusion rates. Early complications included nausea and vomiting in 20.83% of patients; no anastomotic leakage or stenosis was observed. The mean hospital stay was 6.33 days, and only one readmission occurred. Long-term complications included hernias (16.67%) and transient diarrhea, with no cases of chronic diarrhea or bowel obstruction. Conclusion: Our findings indicate that isoperistaltic anastomosis was associated with lower complication rates compared to outcomes for antiperistaltic anastomosis reported in the literature. Notably, reinforced hand-sewn sutures appeared to further improve surgical results and reduce leakage. These observations suggest that reinforcement methods may have a greater impact on outcomes than anastomosis orientation itself. However, larger, controlled studies are necessary to confirm these findings.