Cross-ply unidirectional laminates made of ultra-high molecular weight polyethylene fibers are widely used as components of bullet-proof vests. To simulate the delamination process of the material under penetration, we constructed a numerical mechanical model, which was validated by tests using 7.62 × 39 mm rifle bullets penetrating laminates of different thicknesses. The results show that the delamination region is essentially diamond-shaped. The simulated delamination region is in good agreement with the experimental data. It is found that the delamination region increases with the compression modulus along the fiber direction. The delamination region increases when the shear strength between the fabric layers decreases;However, it is little influenced by the normal strength. The delamination region of the front face of the laminate is little influenced by the failure strain of the material and the initial velocity of the bullet. The delamination region of the back face increases with the failure strain and decreases with the initial velocity.