An understanding of the off-axis mechanical behavior and failure mechanisms of ultra-high molecular weight polyethylene (UHMWPE) cross-ply laminates subjected to quasi-static and dynamic loadings is developed, with focus on the influence of off-axis angle and strain rate. For off-axis tension, UHMWPE laminates exhibit polymer shear response characteristics. An orientation-hardening phenomenon is captured, as fiber rotation leads to local increment of load capacity along the loading orientation. The failure strength presents an evidentially descending trend with off-axis angle from 0° to 45°. A non-monotonic variation of strength with strain rate is further observed: increasing with strain rate up to 500 s−1 but decreasing above, which is attributed to failure mode switching from plastic failure to brittle failure. The Tsai-Wu failure criterion, on homogenized cross-ply laminae, is experimentally modified with rate dependence. Further investigation on detailed information of the unidirectional properties should be conducted with the backing-out scheme to establish unidirectional failure criterion.