This study investigated the stiffness characteristics of crossed-roller bearings (XRBs) subjected to various loading and boundary conditions. A five-degrees-of-freedom XRB model was adopted that considers the effect of roller roundness deformation, which was developed by the authors in a prior study. The analytical formulation for a fully occupied (5 × 5) stiffness matrix of XRB was obtained. Extended simulations were performed to determine the XRB stiffness and internal load distribution considering the effects of the external loads, axial preloads, axial clearance, and angular misalignment. The numerical results confirmed that the bearing stiffness possessed significant nonlinearity with respect to the external loads. Increasing the axial clearance reduced the stiffness of the bearing under radial and moment loading, but it did not affect the stiffness of the pure axially loaded bearing. The stiffness of the bearing with axial clearance increased consistently with the misalignment angle. The stiffness behavior of the preloaded bearing depended on the misalignment angle.