The influence of Cr-Al-Si-N, DLC-Si, and Cr-Al-Si-N/DLC-Si thin coatings deposited on titanium alloy (Ti-Al-Zr-Sn-Nb system) samples with different surface reliefs on wear resistance under abrasion and fretting conditions was investigated. The influence of coatings on the initial microrelief after finishing milling and lapping with micro-grained abrasive was studied by profilometry. The Martens hardness (H) and the elastic modulus (E) were determined through nanoindentation. The H/E ratio was 0.08, 0.09, and 0.13, respectively. The adhesion bond strength and H/E ratio relationship was revealed using a scratch testing analysis. Volumetric wear after 20 min of abrasive exposure was reduced by 11, 25, and 31 times for Cr-Al-Si-N, DLC-Si, and Cr-Al-Si-N/DLC-Si coatings compared to uncoated ones after milling and by 15, 32, and 35 times after lapping. Volumetric wear under fretting conditions was reduced by 1.8 and 4 times for Cr-Al-Si-N coating after milling and lapping. It was reduced by tens of times for DLC-Si coating and by hundreds of times for Cr-Al-Si-N/DLC-Si coating. The Cr-Al-Si-N/DLC-Si coating (a thickness of 3.1 ± 0.15/2.0 ± 0.1 µm) is characterized by the best combination of hardness (24 ± 1 GPa), elastic modulus (185 ± 8 GPa), and friction coefficient (0.04–0.05 after milling and 0.1 after lapping) and ensures maximum wear resistance under a wide range of loads. The novelty of the work is that those coatings were not practically under study concerning the deposition on the titanium alloy regarding typical mechanical loads such as abrasive and fretting wear but are of interest to the aviation and aerospace industry.