In this study, a two-dimensional finite element model is proposed to investigate the wear/fracture mechanisms of polycrystalline cubic boron nitride (PCBN) superabrasives in high-speed grinding process. The special geometric microstructures of PCBN grains are constructed by using the classic Voronoi tessellation technique, and cohesive elements are embedded into the geometric model of PCBN grains as the potential crack propagation paths for simulating the wear/fracture behaviours of PCBN grains under grinding loads. The effects of uncut chip thickness per grain (agmax) on the stress distribution characteristics and wear/fracture behaviours of PCBN grains during grinding are discussed in detail. Results show that the wear behaviour of PCBN grains during grinding mainly occurs around the grain vertex region; however, the fracture behaviour, leading to the quick failure of PCBN grains, is prone to appear around the grain–filler bonding interface, which is usually on the opposite side of the in-feed direction. Moreover, to separate the PCBN grains from the macro-fracture during grinding, the uncut chip thickness per grain should be kept smaller than 1.0 µm to prevent the unfavourable fracture behaviour from appearing around the grain–filler bonding interface. Furthermore, the corresponding single-grain grinding trials are performed to validate the numerical simulation results by evaluating the wear/fracture morphologies of the PCBN superabrasives in the actual grinding operation.