Unidirectional fiber-reinforced plastic (UD-FRP) laminates have been modeled previously as an equivalent quasihomogeneous monoclinic half-space subjected to an inclined line load on the surface using Lekhnitskii’s formulation simulating the orthogonal edge trimming loads in UD-FRPs. In continuation, failure analysis of the aforementioned composite half-space has been carried out in the present investigation based on Tsai–Wu criterion. In particular, the failure behavior of the half-space laminate with respect to the fiber orientation, load inclination angle, and spatial coordinates has been examined in detail. The motivation behind such a study lies in correlating the failure behavior of the half-space laminate with the machining damage observed during orthogonal edge trimming experiments. The present work strives at identifying this relationship and, in the process, understanding the physics of orthogonal cutting of UD-FRP laminates.