This manuscript presents a combined experimental–computational investigation of the compression failure response of laminated composites in double-edge notch compression (DENC) configuration. Analysis of in-situ and post-test DENC experiment results indicates the presence of multiple failure mechanisms, including ply splitting, delamination, and compression kink bands. In order to characterize the onset, growth, and interplay of the critical and subcritical damage mechanisms, a multiscale progressive damage analysis approach is implemented. A nonlocal multiscale damage model explicitly tracks the intraply failure mechanisms that lead to the formation and propagation of kink bands in the specimen. A cohesive zone model is used to track initiation and progression of ply splitting in the specimen. The splitting model was implemented using implicit finite element simulations and deployed with a pre-crack insertion technique to reduce simulation time while preserving prediction accuracy. Model parameters are calibrated based on available calibration data and measurements. The effects of split location and growth characteristics on model predictions are studied. The computational model along with a suite of experiments were employed to study the formation, growth and interactions of damage mechanisms in the composite specimens subjected to compression loading. The onset of matrix damage is not clear from the experimental images but the model predicts early onset around the onset time of splits which greatly reduce the stress concentration at the notches. Analysis of acoustic emission energy experimental data indicate that observable compression failure mechanisms are not causing nonlinearity consistently exhibited in the experiment responses. Simulation results demonstrate the capability of the multiscale modeling approach to predict critical kink bands and sub-critical matrix cracking and splitting in the DENC specimens while reducing computational cost compared to a direct numerical simulation of fibers and matrix.