In this study, the contact fatigue behavior of a PVD TiN coating deposited onto DIN 1.2379 coldwork tool steel is assessed by cyclic spherical indentation. Experimental characterization focuses on the evaluation of critical contact pressures, under both monotonic and cyclic loading, affiliated to the emergence of distinct damage events: circumferential cracking and cohesive spallation at the film or decohesion at the substrate–coating interface. Experimental findings indicate that the coated tool steel studied is susceptible to mechanical degradation under fluctuating contact loads, and the corresponding effective fatigue sensitivity varies depending on the mechanism recalled for defining critical damage.