Ti-5Al-5V-5Mo-3Cr is a near-beta titanium alloy generally employed in the production of high strength parts. Its high tensile strength and light weight, compared to Ti-6Al-4V, make it a suitable choice for landing gear parts and advanced structural components. However, due to its high strength-to-weight ratio, mechanical strength at elevated temperatures, and oxidation resistance, the cutting zone experiences high cutting temperatures, which, combined with a low rate of heat transfer during the machining process, consequently, generates stress, causing premature tool failure. In this paper, several distinct experimental approaches were applied, different machining condition combinations (tools and coolants) were compared, cutting tool wear performance was diagnosed, and, finally, optimized cutting parameters were identified. The main objective of this research was to understand how these parameters affect tribological behavior when machining Ti-5Al-5V-5Mo-3Cr. One of the PCD tools possessed the longest life under high pressure coolant of 28 %–170 % longer than the other tool materials. The main wear mechanism was a combined abrasion, adhesion/attrition, diffusion, and oxidation. Optimizing cooling conditions can affect cutting forces substantially, minimizing residual stress, improving the surface roughness, and reducing the work-hardening during machining. Therefore, the results show that the combination of coolant and cutting tool material leads to longer tool life and improved surface integrity.