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(1) Background: Numerous variables could influence the risk of rectal cancer recurrence or metastasis, and machine learning (ML)-based algorithms can help us refine the risk stratification process of these patients and choose the best therapeutic approach. The aim of this study was to assess the predictive performance of 4 ML-based models for the prediction of local recurrence or distant metastasis in patients with locally advanced low rectal adenocarcinomas who underwent neoadjuvant chemoradiotherapy and surgical treatment; (2) Methods: Patients who were admitted at the first Oncologic Surgical Clinic from the Regional Institute of Oncology, Iasi, Romania were retrospectively included in this study between November 2019 and July 2023. Decision tree (DT), naïve Bayes (NB), support vector machine (SVM), and random forest (RF) were used to analyze imagistic, surgical, and pathological data retrieved from the medical files, and their predictive performance was assessed; (3) Results: The best predictive performance was achieved by RF when used to predict disease recurrence (accuracy: 90.85%) or distant metastasis (accuracy: 89.63%). RF was closely followed by SVM (accuracy for recurrence 87.8%; accuracy for metastasis: 87.2%) in terms of predictive performance. NB and DT achieved moderate predictive power for the evaluated outcomes; (4) Conclusions: Complex algorithms such as RF and SVM could be useful for improving the prediction of adverse oncological outcomes in patients with low rectal adenocarcinoma.