The education sector has benefited enormously through integrating digital technology driven tools and platforms. In recent years, artificial intelligence based methods are being considered as the next generation of technology that can enhance the experience of education for students, teachers, and administrative staff alike. The concurrent boom of necessary infrastructure, digitized data and general social awareness has propelled these efforts further. In this review article, we investigate how artificial intelligence, machine learning, and deep learning methods are being utilized to support the education process. We do this through the lens of a novel categorization approach. We consider the involvement of AI-driven methods in the education process in its entirety—from students admissions, course scheduling, and content generation in theproactiveplanning phase to knowledge delivery, performance assessment, and outcome prediction in thereactiveexecution phase. We outline and analyze the major research directions under proactive and reactive engagement of AI in education using a representative group of 195 original research articles published in the past two decades, i.e., 2003–2022. We discuss the paradigm shifts in the solution approaches proposed, particularly with respect to the choice of data and algorithms used over this time. We further discuss how the COVID-19 pandemic influenced this field of active development and the existing infrastructural challenges and ethical concerns pertaining to global adoption of artificial intelligence for education.