Indiana University-Purdue University Indianapolis (IUPUI) / A procedure for calibrating a discrete element (DE) computational soil model for various moisture contents using a conventional Asperity-Spring friction modeling technique is presented in this thesis. The procedure is based on the outcomes of two physical soil experiments: (1) Compression and (2) unconfined shear strength at various levels of normal stress and normal pre-stress. The Compression test is used to calibrate the DE soil plastic strain and elastic strain as a function of Compressive stress. To calibrate the DE inter-particle friction coefficient and adhesion stress as a function of soil plastic strain, the unconfined shear test is used. This thesis describes the experimental test devices and test procedures used to perform the physical terramechanical experiments. The calibration procedure for the DE soil model is demonstrated in this thesis using two types of soil: sand-silt (2NS Sand) and silt-clay(Fine Grain Soil) over 5 different moisture contents: 0%, 4%, 8%, 12%, and 16%. The DE based models response are then validated by comparing them to experimental pressure-sinkage results for circular disks and cones for those two types of soil over 5 different moisture contents. The Mean Absolute Percentage Error (MAPE) during the compression calibration was 26.9% whereas during the unconfined shear calibration, the MAPE was calculated to be 11.38%. Hence, the overall MAPE was calculated to be 19.34% for the entire calibration phase.