Legal predictability is one of the essential indicators of an efficient private law system because it enables contracting parties to estimate legal consequences before disputes arise. In the Iranian legal system, contractual damages are governed by statutory provisions, judicial interpretation, and evolving judicial practice. Nevertheless, differences in judicial reasoning and the absence of unified interpretative standards have generated considerable uncertainty regarding the determination and enforcement of contractual damages. This study investigates the level of legal predictability of contractual damages in Iranian private law through an empirical evaluation of published judicial decisions together with statutory principles governing contractual liability. A doctrinal-empirical research design was employed by integrating qualitative legal analysis with systematic examination of judicial decisions issued by Iranian civil courts and the Supreme Court. Legislative provisions of the Iranian Civil Code were analyzed alongside judicial reasoning and interpreted within comparative contract law frameworks. The findings indicate that statutory provisions provide a relatively coherent legal foundation, whereas judicial predictability is primarily influenced by variations in judicial interpretation concerning causation, foreseeability, contractual intent, and proof of damages. Comparative legal principles demonstrate that greater interpretative consistency could significantly improve legal certainty without requiring extensive legislative reform. The study contributes practical recommendations for strengthening judicial consistency, enhancing contractual certainty, and improving the overall predictability of contractual remedies in Iranian private law while providing a structured analytical framework applicable to future empirical legal studies.