Rolling-element bearings are the most commonly used components in all rotating machinery. The variations in the operating conditions such as an increase in the number of operating cycles, load, speed, service temperature, and lubricant degradation result in the development of various defects such as pitting, spalling, scuffing, scoring, etc. The defects that appeared on rolling contact surfaces cause surface deterioration and change in the vibration and sound levels of the bearing system. The present experimental investigations are aimed at assessing the surface fatigue wear that appears on the contact surfaces of roller bearings. The studies considered the estimation of specific film thickness, analysis of surface fatigue wear developed on the rolling-element surfaces, surface roughness analysis, grease degradation analysis using Fourier transform infrared radiation, and vibration and sound signal measurement and analysis. The results obtained from the experimental investigation provide a good correlation between surface wear, vibration, and sound signals with a transition in the lubrication regimes in the Stribeck curve.