(1) Background: Data suggest that patients with coronary chronic total occlusion (CTO) managed with percutaneous coronary intervention (PCI) could have better outcomes than those treated with optimal medical therapy alone. We aimed to systematically review dedicated scoring systems used to predict successful PCI in patients with CTO. (2) Methods: Electronic databases of MEDLINE (PubMed), Embase, and Cochrane were searched. (3) Results: 32 studies were included. We provided insights into all available predictive models of PCI success in CTO including predictive performance, validations, and comparisons between different scores and models’ limitations. Considering the differences in the population included, coronary lesions, and techniques applied across clinical studies, the most used scores displayed a modest to good predictive value, as follows: J-CTO (AUC, 0.55–0.868), PROGRESS-CTO (AUC, 0.557–0.788), CL (AUC, 0.624–0.800), CASTLE (AUC, 0.633–0.68), and KCCT (AUC, 0.703–0.776). As PCI for CTO is one of the most complex interventions, using dedicated scoring systems could ensure an adequate case selection as well as preparation for an appropriate recanalization technique in order to increase chances of successful procedure. (4) Conclusion: Clinical models appear to be valuable tools for the prediction of PCI success in CTO patients. Clinicians should be aware of the limitations of each model and should be able to correctly select the most appropriate score according to real-life case particularities such as lesion complexity and operator experience in order to maximize success and achieve the best patients’ outcomes.