The focus of this study is exploring a scale-span modeling method to simulate the structural mechanical responses and dynamic progressive failure behaviors of carbon fiber reinforced plastics (CFRPs) in drilling. A dynamic progressive failure theory based on modified micromechanics of failure (MMF) criterion with new damage evolution laws was first introduced for intralaminar damage. The relationship between macroscopic stress and microscopic stress was established by the stress amplification factors (SAFs). Meanwhile, an auxiliary deleting element criterion was introduced to delete the serious distortion elements for the sake of preventing nonconvergence of the simulation model, and the bilinear cohesive model with mixed-mode failure criterion was employed to simulate the interlaminar delamination. Then, the drilling behaviors of T700S-12 K/YP-H26 CFRPs using a tapered drill-reamer (TDR) were simulated based on the established scale-span theory model which is implemented by user-defined material subroutine VUMAT built on ABAQUS/Explicit platform. Finally, a series of experiments were performed to validate correctness of the simulation results from the perspectives of hole-making quality evaluation index. Results show that the established scale-span simulation model is shown to agree reasonably well with the experiments, and different kinds of damage behavior of the prefabricated hole can be truly simulated in drilling CFRPs.