Bearings are used to reduce friction between two rolling /sliding members of the machines. Under normal operating conditions, an increase in the fatigue load cycles on the bearing contact surfaces results in surface defects viz. micro pitting, macro pitting, spalling and scuffing, thereby causing lubricant degradation. Hence, to maintain a better operating performance of rotating machines, it is essential to keep track of operating parameters. This paper describes the results of experimental investigations carried out to assess wear propagation on bearing contact surfaces using tribological and vibration parameters. Results obtained from experimental investigations provide a good correlation between the increase in surface fatigue wear and corresponding effects on transition in lubrication regimes, increased vibration levels, variations in rheological properties of lubricant and wear mechanisms developed on the contact surfaces of the roller bearing. The proposed approach can be used as a promising tool to assess incipient faults developed in roller bearing.