Cr12MoV die steel is a typical high-strength and high-hardness material. Because of the high hardness of Cr12MoV die steel, which is approximately 50–65 HRC after quenching, and the tool’s weak rigidity, cutting vibration, and tool deformation are inevitable during the cutting process. In this paper, a model for predicting the surface topography of a convex curved die steel machined by a ball-end milling cutter was established. In addition, the surface springback of the workpiece is considered. According to the surface characteristics of the convex curved workpiece, the vector algorithm and transformation matrix are applied to calculate the milling cutter motion trajectory equation. Then, the influence of dynamic factors on the tool path is calculated, and finally the surface topography of the workpiece is simulated through the Z-map model. The simulation error of three-dimensional surface roughness Sa at different positions of the curved surface is between 10% and 16%. After considering the dynamic factors, the simulation error is reduced by about 50%.