Numerical modeling of bones is necessary for design of efficient surgical cutting tools that can provide low cutting forces, reduce damage and prevent thermal necrosis of bone tissue. Development of realistic numerical models of cortical bone tissue requires deep knowledge of its deformation behaviour. Deformation mechanisms of bones differ from those of metals, polymers and composites since bones consist of a living tissue with hierarchical microstructure. The aim of this study is to analyse deformation characteristics of the cortical bone tissue from both experimental and numerical perspectives. Initially, Vickers hardness tests were conducted at various anatomical positions on a cross-section of a bovine femur bone to observe location-based variation of its mechanical response. Various load magnitudes ranging between 1 kgf and 100 kgf were applied in the Vickers hardness tests to analyse the effect of anisotropy on damage evolution. These tests were simulated using a finite element scheme to reproduce the mechanical behaviour of bones in indentation. Finally, results of the hardness tests were compared with those obtained from finite element simulations.