Risks and uncertainties are inevitable in construction projects and can drastically change the expected outcome, negatively impacting the project’s success. However, risk management (RM) is still conducted in a manual, largely ineffective, and experience-based fashion, hindering automation and knowledge transfer in projects. The construction industry is benefitting from the recent Industry 4.0 revolution and the advancements in data science branches, such as artificial intelligence (AI), for the digitalization and optimization of processes. Data-driven methods, e.g., AI and machine learning algorithms, Bayesian inference, and fuzzy logic, are being widely explored as possible solutions to RM domain shortcomings. These methods use deterministic or probabilistic risk reasoning approaches, the first of which proposes a fixed predicted value, and the latter embraces the notion of uncertainty, causal dependencies, and inferences between variables affecting projects’ risk in the predicted value. This research used a systematic literature review method with the objective of investigating and comparatively analyzing the main deterministic and probabilistic methods applied to construction RM in respect of scope, primary applications, advantages, disadvantages, limitations, and proven accuracy. The findings established recommendations for optimum AI-based frameworks for different management levels—enterprise, project, and operational—for large or small data sets.