Simulation of tool-to-soil interaction provides opportunities to accelerate new equipment design and evaluate performance of tillage tools. Simulation based evaluation of worn tillage tools performance on soil flow has not been done. Discrete Element Modelling (DEM) has a potential to simulate worn tool to soil interaction problems, where worn tools CAD can be generated using 3D scanning. The DEM parameters of Hertz-Mindlin with Parallel Bond model were calibrated to match draft force and soil failure zone measured from a tool bar moving at 0.22 m/s and 38 mm cutting depth. The draft force and soil forward failure zone were predicted at 7% and 24% relative errors compared to measured values, respectively. Using the optimized DEM soil model, the interaction of three 3D reconstructed sweeps (new sweep, carbide treated-worn, untreated-worn) with soil were simulated to compare their geometric wear dimensional loss, performance on soil forces and soil flow. Results showed that the carbide treated-worn sweep had similar soil draft force and soil forward failure distance as the new sweep. The untreated-worn sweep showed lower vertical force (less suction) and its wing induced soil failure zone (front and lateral) showed poor soil tilth quality compared with the carbide treated-worn sweep and the new sweep.