This chapter explores the evolution of computer-aided design (CAD) in civil engineering by examining studies from the early manual drafting era to the integration of computers in design processes. It categorizes 73 historic works based on sub-disciplines such as structural, geotechnical, hydraulic, and transportation engineering. The study highlights the transition from labor-intensive manual methods to efficient, computer-based practices, showing how early computational tools shaped today’s modern CAD systems. It serves as a valuable resource for understanding the roots and milestones of digital transformation in engineering design.