Background: Anastomotic leakage (AL) remains one of the most feared complications after colorectal surgery. This study aims to identify preoperative risk factors for AL using a five-year dataset from two Romanian surgical clinics. Matherial and Methods: A retrospective cohort of 155 patients undergoing colorectal resection with primary anastomosis (105 from “Colentina” Hospital and 50 from “Dr. I. Cantacuzino” Hospi-tal) was analyzed. Preoperative demographic, clinical, and laboratory data were ex-tracted and assessed using univariate and multivariable logistic regression. Statistical analyses were performed using IBM SPSS. Results: The overall AL rate was 10.3%. Multivariable analysis identified high ASA class (OR 17.6; p = 0.001), emergency sur-gery (OR 32.2; p = 0.0007), and heavy alcohol use (OR 15.3; p = 0.004) as independent predictors of leakage. While low preoperative albumin and smoking were associated with leakage in bivariate analysis, these did not remain significant after adjustment. Notably, all laboratory markers were based on preoperative values, distinguishing our approach from prior studies that commonly evaluate postoperative biomarkers. No statistically significant effect was found for neoadjuvant chemotherapy or radiother-apy after controlling for other covariates. Conclusions: High ASA score, alcohol abuse, and emergency surgery were the strongest independent predictors of AL in our cohort. The lack of predictive power of certain widely reported factors, such as low albumin, may reflect our dataset’s focus on preoperative optimization. These findings support the use of individualized risk assessment and reinforce the role of preoperative prepa-ration in reducing leak incidence in colorectal surgery.