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When a shield tunneling machine based on earth pressure balance (EPB) bores through the sandy pebble stratum, the conditioned sandy pebble inside the soil cabin of shield machine is an aggregation of numerous granules with pebble grains as skeleton. It is essential to construct a reasonable particle element model of the conditioned sandy pebble before carrying out discrete element simulation of the soil cabin system. Sandy pebble belongs to a kind of frictional material, the friction behavior of which is highly sensitive to the angularity of the grains. In order to take the shape effect into account, two particle element models—single sphere with rolling resistance and cluster of particles—were attempted in this paper. The undetermined contact parameters in two models were calibrated by virtue of least squares support vector regression machine (LS-SVR). With the purpose of making both the flow behavior and mechanical properties of the modeled soil consistent with reality, the calibration targets the result of laboratory test of slump test and large-scale triaxial test as goals. The presented comparative analysis indicates that the two established particle models both can well describe the strength property and fluidity of the actual soil due to properly calibrated parameters. So, the rolling resistance and cluster models are two effective ways to incorporate the shape effect. Besides, because of the angularity of the nonspherical grains, there exists strong interlocking between clusters. So, in the cluster model, relatively smaller rolling friction coefficient and surface energy are required. It is also concluded that the single sphere model is more computationally efficient than the cluster model.