This study investigated the relationships between trabecular microstructure and elastic modulus, compressive strength, and suture anchor pullout strength. Twelve fresh-frozen humeri underwent mechanical testing followed by micro-computed tomography (μCT). Either compression testing of cylindrical bone samples or pullout testing using an Arthrex 5 mm Corkscrew was performed in synthetic sawbone or at specific locations in the humerus such as the greater tuberosity, lesser tuberosity, and humeral head. Synthetic sawbone underwent identical mechanical testing and μCT analysis. Bone volume fraction (BVF), structural model index (SMI), trabecular thickness (TbTh), trabecular spacing (TbSp), trabecular number (TbN), and connectivity density were compared against modulus, compressive strength, and pullout strength in both materials. In cadaveric bone, modulus showed correlations to all of the microstructural properties, while compressive and pullout strength were only correlated to BVF, SMI, and TbSp. The microstructure of synthetic bone differed from cadaveric bone as SMI and TbTh showed little variation across the densities tested. Therefore, SMI and TbTh were the only microstructural properties that did not show correlations to the mechanical properties tested in synthetic bone. This study helps identify key microstructure–property relationships in cadaveric and synthetic bone as well as illustrate the similarities and differences between cadaveric and synthetic bone as biomechanical test materials.