Over the past 25 years, the Leadership in Energy and Environmental Design (LEED) system has evolved into an international green building rating system, transforming the evaluation and rating of green buildings. Simultaneously, the green building sector has adopted more digital technologies, facilitating data-driven decisions for building performance evaluation, rating, and automation. This study traces LEED development and its integration with different digital technologies over the past quarter-century by examining how digital tools have supported LEED’s implementation. A systematic review methodology framework based on the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) is employed to filter 202 publications based on research questions. The findings reveal key lessons from the incorporation of digital technologies in facilitating design decision-making under the LEED rating system and show its evolution from inflexible templates toward cutting-edge technologies like Building Information Modeling (BIM), Artificial Intelligence (AI), and Digital Twins (DT). The integration of these technologies has streamlined building performance assessment, enabled real-time monitoring, and facilitated predictive analysis. This study presents insightful data on the contribution of digital technologies towards augmenting the processes of LEED, illustrating theoretical implications and new views. These outcomes lay the basis for general innovation in green building rating systems, fostering sustainability and efficiency in the built environment.