This study develops a computational framework to predict the evolution of matrix cracking and the resulting interlaminar delamination in cross-ply composite laminates subjected to in-plane loading. By combining meso–macro multiscale modeling with continuum damage mechanics (CDM), an integrated approach is proposed to evaluate progressive damage in composite structures. The methodology employs quasi-simultaneous multiscale analysis, advanced finite element simulations, and image-processing-assisted machine learning to accurately characterize the initiation and propagation of matrix cracks and delamination. To quantify the influence of matrix cracking and interlaminar separation on the nonlinear response of multilayer laminates, a simplified AI-based formulation is developed to compute damage parameters linked to matrix cracking and induced delamination. A CDM-based user subroutine is implemented in the finite element environment to simulate the gradual evolution of transverse cracks, fiber breakage, and interlayer separation, enabling prediction of the ultimate failure load under monotonic loading. The accuracy of the proposed computational model is validated against available experimental datasets. The predicted stress–strain curves, damage chronology, and failure patterns show excellent agreement with experimental observations, confirming the method's ability to capture intralaminar and interlaminar damage mechanisms simultaneously in composite laminates.