The contact mechanics is an important aspect in tool-based micromachining but a complete solution is not yet available. In this paper, a novel finite element analysis using arbitrary Lagrangian-Eulerian method and a special experimental setup using a high-speed and low field-of-view photography technique are used for the study of the contact problem. Discussions are emphasized on the interrelationship between shear contacts and material separation, the effect of contact pressure on the stick-slide behavior and the analysis of tool-chip contact length. The results revealed that material separation correlates to the stagnation phenomenon which is reflected from the shear contact vector while sticking and sliding is highly influenced by the distributions of contact pressure. Moreover, a non-dimensional solution for the contact length of micromachining is proposed based on the numerical and experimental results.