Owing to high specific strength and designability, unidirectional carbon fiber reinforced polymer (UD-CFRP) has been utilized in numerous fields to replace conventional metal materials. Post machining processes are always required for UD-CFRP to achieve dimensional tolerance and assembly specifications. Due to inhomogeneity and anisotropy, UD-CFRP differs greatly from metal materials in machining and failure mechanism. To improve the efficiency and avoid machining-induced damage, this paper undertook to study the correlations between cutting parameters, fiber orientation angle, cutting forces, and cutting-induced damage for UD-CFRP laminate. Scanning acoustic microscopy (SAM) was employed and one-/two-dimensional damage factors were then created to quantitatively characterize the damage of the laminate workpieces. According to the 3D Hashin’s criteria a numerical model was further proposed in terms of the finite element method (FEM). A good agreement between simulation and experimental results was validated for the prediction and structural optimization of the UD-CFRP.