An experimental investigation was conducted in this work to analyze the effect of the workpiece microstructure on tool wear behavior and stability of the cutting process during marching difficult to cut titanium alloys: Ti–6Al–4V and Ti-555. The analysis of tool–chip interface parameters such as friction, temperature rise, tool wear and workpiece microstructure evolution under different cutting conditions have been investigated. As the cutting speed increases, mean cutting forces and temperature show different progressions depending on the considered microstructure. Results show that wear modes of cutting tools used for machining the Ti-555 alloy exhibit contrast from those obtained for machining the Ti–6Al–4V alloy. Because of the fine-sized microstructure of the near-β titanium Ti-555, abrasion mode was often found to be the dominate wear mode for cemented cutting tools. However, adhesion and diffusion modes followed by coating delamination process were found as the main wear modes when machining the usual Ti–6Al–4V alloy by the same cutting tools. Moreover, a deformed layer was detected using SEM–EDS analysis from the sub-surface of the chip with β-grains orientation along the chip flow direction. The analysis of the microstructure confirms the intense deformation of the machined surface and shows a texture modification.