Tool wear plays a decisive role in achieving the required surface quality and dimensional accuracy during the machining of Inconel 718-based products. The highly stochastic phenomenon of tool wear, particularly in later stages, results in difficulty in predicting the failure point of the tool. The present research work aims to study this late-stage wear of the tool by generating consistent wear conditions and thereby decoupling the late-stage wear from the wear history. To do so, a multi-axis grinding operation is employed to create artificial tool wear that replicates the topology of natural wear occurring in the process. In order to evaluate the imitating ability of the proposed methodology, microscopic images in different wear states of naturally and contrived worn tools were analyzed. The methodology was validated by comparing the resulting process forces measured during end milling with the natural and contrived worn tool for different path strategies. Finally, a qualitative finite element (FE) analysis was conducted, and specific force coefficients for worn tool segments were determined through simulation.