Cracking processes in brittle amorphous polymers within sliding contacts and their relationships with bulk fracture properties are reviewed. The focus is on the use of model single asperity contacts to mimic and characterize the failure modes which can be encountered at the microasperity level during the wear of macroscopic rough contacts between polymer surfaces and rigid counterfaces. Using the resources of in situ contact visualization, crack initiation and propagation mechanisms within epoxy substrates are detailed under contact fatigue conditions. With the prospect of understanding the fundamental mechanisms involved in particles detachment from brittle polymer surfaces, it is shown how cracks locations, orientations and depths can be predicted from a knowledge of the bulk toughness and fatigue properties of the polymer by means of a fracture mechanics analysis of the contact. In the last section, the sensitivity of contact fatigue processes to molecular parameters is addressed in the case of anti-plasticized epoxy networks and random copolymers of poly(methylmethacrylate).