The discrete singular convolution (DSC) algorithm is used to analyze the deflection and free vibration behavior of a simply supported anisotropic rectangular plate. A novel approach is proposed to solve the difficulty in using DSC to handle the simply supported boundary conditions with bending–twisting coupling. DSC results are presented for bending under distributed load and a center concentrated load, and natural frequencies of flexural vibrations. It is shown that the DSC with proposed method to apply the simply supported boundary conditions yields very accurate results as compared to exact solutions or results obtained by methods of differential quadrature and finite element with fine meshes. It is also verified that neglecting the bending–twisting coupling in applying the simply supported boundary conditions may result incorrect solutions, especially for the bending analysis of anisotropic plates.