The primary purpose of this paper is to outline a methodology for evaluating the likelihood of cortical bone fracture in the proximal femur in the event of a sideways fall. The approach includes conducting finite element (FE) analysis in which the cortical bone is treated as an anisotropic material, and the admissibility of the stress field is validated both in tension and compression regime. In assessing the onset of fracture, two methodologies are used, namely the Critical Plane approach and the Microstructure Tensor approach. The former is employed in the tension regime, while the latter governs the conditions at failure in compression. The propagation of localized damage is modeled using a constitutive law with embedded discontinuity (CLED). In this approach, the localized deformation is described by a homogenization procedure in which the average properties of cortical tissue intercepted by a macrocrack are established. The key material properties governing the conditions at failure are specified from a series of independent material tests conducted on cortical bone samples tested at different orientations relative to the loading direction. The numerical analysis deals with simulations of experiments involving the sideways fall, and the results are compared with the experimental data. This includes both the evolution of fracture pattern and the local load-displacement characteristics. The proposed approach is numerically efficient, and the results do not display a pathological mesh-dependency. Also, in contrast to the XFEM approach, the analysis does not require any extra degrees of freedom.