A multiscale analysis of the mechanical behavior of bovine Haversian cortical bone is presented in the frame-work of linear elasticity. Cortical bone displays a complex microstructure that includes four phases: Haversian canals, osteons, cement lines, and interstitial bone. Based on close experimental observations, a Monte Carlo algorithm is implemented to build the natural bone composite microstructure. To represent the hierarchical nature of bone, the algorithm incorporates macroscopic morphological components, such as its porosity and osteonal volume fraction, as well as microscopic parameters, such as the characterized distributions of the osteons diameters. Bone local mechanical properties are measured by nanoindentation and microextensometry. The three-dimensional microstructures are discretized by a finite element method in order to evaluate the representative volume element of bovine cortical bone. The numerical model calculates the macroscopic bulk and material Young’s moduli and describes the local stress and strain. How geometrical or mechanical factors affect bone failure is investigated through a comparison of the macroscopic anisotropy and local strain to experimental data.