The basic hypothesis of this article focuses on the study of cutting tool wear with regard to the elimination of occurrence of poor-quality holes when drilling into new austenitic stainless steel. The problem of drilling holes with diameter D=3 to 10 mm resides in the fact that 20 to 30% of these holes do not comply with prescribed requested requirements. This article presents the results of experiments focusing on the study of the damage process in screw drills with diameter d=6.0 mm when drilling into new austenitic stainless steel X02Cr18Ni10MoTiN. This study also includes an analysis of accompanying phenomena in the cutting zone by measuring some selected parameters. The results of the experiments were compared with Cr18Ni8 steel and then verified when drilling holes into specific products.