Understanding the evolution of frictional interface state is of great significance to the effective design of antifriction and wear resistance properties at macro-scale contact, which plays an important role in the whole tribological performance. The trigological behavior of the sintered polycrystalline diamond (PCD) sliding against different mating materials was evaluated under dry nitrogen (N2) environment. The coefficients of friction (COF) and wear rates of the PCD were diverse due to the various formations of transferflim and filling effects across sliding interfaces, which is dependent on the mating materials. Additionally, the Raman measurements demonstrate that the carbon rehybridization (sp3 to sp2) process occurred accompanying with the formation of carbonaceous transferfilm during sliding. The effects of antifriction transferfilm formations and filling on the enhanced tribological performance of PCD at macro-scale contact were highlighted.