Tailoring a material’s properties for low friction and little wear in a strategic fashion is a long-standing goal of materials tribology. Plastic deformation plays a major role when metals are employed in a sliding contact; therefore, the effects of stacking fault energy and mode of dislocation glide need to be elucidated. Here, we investigated how a decrease in the stacking fault energy affects friction, wear, and the ensuing sub-surface microstructure evolution. Brass samples with increasing zinc concentrations of 5, 15, and 36 wt% were tested in non-lubricated sphere-on-plate contacts with a reciprocating linear tribometer against Si3N4 spheres. Increasing the sliding distance from 0.5 (single trace) to 5,000 reciprocating cycles covered different stages in the lifetime of a sliding contact. Comparing the results among the three alloys revealed a profound effect of the zinc concentration on the tribological behavior. CuZn15 and CuZn36 showed similar friction and wear results, whereas CuZn5 had a roughly 60% higher friction coefficient (COF) than the other two alloys. CuZn15 and CuZn36 had a much smaller wear rate than CuZn5. Wavy dislocation motion in CuZn5 and CuZn15 allowed for dislocation self-organization into a horizontal line about 150 nm beneath the contact after a single trace of the sphere. This feature was absent in CuZn36 where owing to planar dislocation slip band-like features under a 45° angle to the surface were identified. These results hold the promise to help guide the future development of alloys tailored for specific tribological applications