An experimental investigation was focused on the failure behavior of unidirectional fiber-reinforced polymers when subjected to combined longitudinal/transverse compression and in-plane shear due to off-axis loading. Block-shaped and end-loaded specimens, spanning ten different fiber orientations (0°, 5°, 10°, 15°, 20°, 30°, 45°, 60°, 75°, and 90° with respect to the loading direction), were loaded to ultimate failure using a dedicated fixture. Different failure modes, including longitudinal compression, in-plane shear, and transverse compression, were identified, along with distinctive characteristics of the corresponding failure envelopes. Four physically based failure theories-Hashin, Camanho, Puck, and LaRC05-were subjected to a comparative analysis. Criteria derived from the concept of the action plane consistently outperformed in describing matrix-dominated failures, providing both qualitative and quantitative predictions of failure stresses and fracture plane orientation. However, for fiber-dominated failures, these theories seem to fall short in providing satisfactory predictions, particularly in accurately describing the influence of shear on fiber compression failure. Although criteria based on fiber-kinking theory can reasonably explain the formation of kink bands, they tend to yield overly conservative results. Recalibrations and minor refinement based on experimental results were implemented, leading to an improved agreement. Finally, the constructive role of off-axis compression tests in characterizing the failure behavior of unidirectional composites is discussed.