Automation and on-machine manufacturing process measurement is essential in increasing product productivity. However, a significant challenge is the radial Fresnel lens structure-array machining and on-machine measurement research for a large-scale roller mold. We present a rotating A-axis machining method for manufacturing an array of a radial Fresnel lens structure, based on an ultraprecision four-axis drum roll lathe system developed by the team. Therefore, based on the principle of a virtual multiprobe, the traditional two-point method is improved and applied to the on-machine measurement of the radial Fresnel lens structure of the roll mold. Through the machining and on-machine measurement experiments of the radial Fresnel lens structure of the roller mold, the feasibility of the machining method and measurement method is verified.