In this study, undulations and their influence on the longitudinal compressive strength of a unidirectional glass fiber reinforced polymer (GFRP) composite are investigated theoretically and experimentally. The objective of this research is to explore the failure mechanisms in FRP and to characterize the mechanical properties of FRP as a function of fiber orientation. For this purpose, a multiscale material model is developed that considers a stochastic fiber orientation distribution (FOD) and models matrix fracture-initiated failure. The relationship between compressive strength and undulation is investigated experimentally on standardized specimens made of unidirectional GFRP. The fiber orientations are measured using X-ray computed tomography and ImageJ image analysis, resulting in a binormal distribution of fiber orientations in the series of samples tested. To examine the failure process in detail, the compression tests are simulated using finite element analysis (FEA). Both the FEA results and the measured compressive strengths confirm the model assumption of matrix fracture-initiated failure under longitudinal compressive loading. The presented analytical model realistically represents the correlation of compressive strength with the FOD.