Colon leakage score (CLS) was introduced as a clinical tool to predict anastomotic leakage (AL) in patients who underwent left-sided colorectal surgery, but its clinical validity has not been widely studied. We evaluated the clinical utility of CLS and developed a modified CLS (m-CLS). In total, 566 patients who underwent left-sided colorectal surgery were enrolled and categorized into training (n = 396) and validation (n = 170) sets via random sampling. Using CLS variables, the least absolute shrinkage and selection operator (LASSO) regression model was applied for variable selection and predictive signature building in the training set. The model’s performance was validated in the validation set. The predictive powers of m-CLS and CLS were compared by the area under the receiver operating characteristic (AUROC) curve in the overall group. Twenty-three AL events (4.1%) were noted. The AL group had a significantly higher mean CLS than the No Leakage group (12.5 vs. 9.6, p = 0.001). Five clinical variables were selected and used to generate m-CLS. The predictive performance of m-CLS was similar in training and validation sets (AUROC 0.838 vs. 0.803, p = 0.724). In the overall set, m-CLS was significantly predictive of AL and performed better than CLS (AUROC 0.831 vs. 0.701, p = 0.008). In conclusion, LASSO-model-generated m-CLS could predict AL more accurately than CLS.