Multi-scale bedding fractures, i.e., km-scale regional bedding fractures and cm-scale lamina-induced fractures, have been the focus of unconventional oil and gas exploration and play an important role in resource exploration and drilling practice for tight oil and gas. It is challenging to conduct numerical simulations of bedding fractures due to the strong heterogeneity without a proper mechanical criterion to predict failure behaviors. This research modified the Tien–Kuo (T–K) criterion by using four critical parameters (i.e., the maximum principal stress (σ1), minimum principal stress (σ3), lamina angle (θ), and lamina friction coefficient (μlamina)). The modified criterion was compared to other bedding failure criteria to make a rational finite element simulation constrained by the four variables. This work conducted triaxial compression tests of 18 column samples with different lamina angles to verify the modified rock failure criterion, which contributes to the simulation work on the multi-scale bedding fractures in the statics module of the ANSYS workbench. The cm-scale laminated rock samples and the km-scale Yanchang Formation in the Ordos Basin were included in the multi-scale geo-models. The simulated results indicate that stress is prone to concentrate on lamina when the lamina angle is in an effective range. The low-angle lamina always induces fractures in an open state with bigger failure apertures, while the medium-angle lamina tends to induce fractures in a shear sliding trend. In addition, the regional bedding fractures of the Yanchang Formation in the Himalayan tectonic period tend to propagate under the conditions of lower maximum principal stress, higher minimum principal stress, and larger stratigraphic dip.