This paper reports a study of the evolution of directional texture and its role in the manipulation of tribofilm layers under boundary lubrication (BL). The use of surface protective tribofilms/lubricant chemistries along with the use of textured surfaces has gained significant attention as an effective BL strategy to provide advanced lubrication. However, the evolution of surface texture in the direction of motion under continuous asperity-to-asperity contact remains unexplored, especially in correlation with the tribofilm properties on textured surfaces. Mechanical polishing using SiC abrasive paper was used to generate directional and concentric surface texture on 52100 steel discs. Tribological tests of varying time durations were performed using MoS2-based lubricant to systematically study the evolution of texture and tribofilm using a pin-on-disc rotational setup. A laser microscope was used for areal texture characterization while tribofilm was characterized using SEM/EDS, Raman, and FIB/TEM. The results show that directional texture manipulates the early onset and tribo-chemical reactions and the delivery of lubricant tribofilm on the asperities during the evolution process.