Laminates of angled unidirectional carbon-fiber-reinforced plastics are often used in designing structures. Singularities appear in the interlaminar area of the free edge because of differences in elastic properties between plies. We investigate the initial cracking of angle-ply laminates using numerical simulations considering the free-edge effect. Multiscale modeling is applied to predict initial cracking of angle-ply laminates. This multiscale modeling consists of a macroscopic laminate scale assuming a homogeneous body and a microscopic structural scale consisting of some fibers and matrix resin. On a macroscopic scale, each ply of angle-ply CFRP laminates is modeled as a homogeneous body, and 3D finite-element analyses are performed to predict singular strain fields of the free edge. An elasto-plastic constitutive model based on the Sun and Chen model is applied for unidirectional CFRP to represent the strong nonlinear behavior of the free edge. On a microscopic scale, 3D periodic unit cell analyses are performed by application of the macroscopic strain fields obtained by homogeneous laminate analyses. A damage growth model based on continuum damage mechanics is applied for matrix resin, and the initial cracking of angle-ply laminates is predicted based on the calculated damage. Simulated results are compared with experiment results reported by Ogihara et al.