Particle breakage of granular materials under cyclic shearing is related to a variety of engineering problems in geotechnical and transportation engineering. However, there is limited understanding regarding the detailed evolution law of breakage under cyclic shearing. To this end, a series of cyclic simple shear tests were conducted on artificially dyed gypsum particles. It was observed that, in contrast to the particle size distribution of the whole sample, the fractional particle size distributions of gap-graded samples followed a unified breakage evolution path as those of the uniformly graded ones and tended towards fractional fractal distributions. These results have inspired the introduction of the fractional breakage index. Moreover, the breakage-plastic work relationship was further extended to describe the breakage of fractional particles, incorporating the effect of the number of cycles on the plastic work distribution. Finally, based on the concept of breakage-packing, a predictive model for plastic work-breakage-deformation of crushable granular materials under cyclic shearing was proposed. These results have the potential in understanding the detailed particle breakage evolution and establishing a predictive framework for the breakage-induced deformation of crushable granular materials.