Wear particles generated due to the relative sliding of the roll and the sheet metal in the roll bite are one of the main factors that contaminate the surface of a cold rolled steel sheet. The details of the wear mechanisms in the contact of individual roll-sheet asperities define the total amount of wear particles generated. In this paper, a micro-mechanical experimental approach is coupled with material point method (MPM) scratch simulations to study the friction and wear behavior of a single roll asperity sliding through a sheet metal. Micro-tribology experiments in the form of single asperity scratch testing showed that ploughing is the dominant wear mechanism in lubricated conditions, while wedge forming was the main wear mechanism in the absence of lubricant. The beneficial influence of chrome plating the rolls on wear particles formation is found to stem from its interaction with the lubricant as the same influence was not observed in non-lubricated test conditions. MPM single asperity simulations revealed that almost all the frictional resistance arises from deforming the substrate in the case of an interfacial shear strength corresponding to the lubricated contact. In contrast, MPM showed that, in unlubricated sliding, the frictional resistance is primarily due to shearing of the adhesion junction and tearing the deforming body. Furthermore, using the degree of wear of the scratch experiments as a benchmark, a critical plastic strain needed to produce wear particles was found to be between 3 to 4 for the investigated interstitial-free steel.