Punching of ultra-high-strength spring steel causes critical stresses in the tools. Pronounced wear and even spontaneous failure may occur. Wear of the punches influences the quality of the cutting surfaces of the blanked parts, which is predominantly determined by the cutting edge radius. The radius differs with an increasing number of strokes depending on the punch material. However, there are no studies characterizing the influence of the cutting edge radius on the cutting surface quality on an industrial scale, i.e., considering a very high number of strokes. In the presented study, punches made of high-speed steel, powder metallurgical steel and carbide were used to punch the ultra-high-strength steel 1.4310 (Rm = 1824 MPa) up to 1,000,000 strokes. The experiments were stopped at defined number of strokes, the punches were removed, nondestructively characterized regarding cutting edge radius and wear and reinstalled. It turned out that the radius differed significantly over the number of strokes and, further, varied depending on the punch material. Remarkably, the most low-cost material, precisely the high-speed steel, showed the smallest cutting edge radius of 16 µm and brought the parts with the best cutting surface quality (more than 30% burnish zone) after the maximum number of strokes. The results indicate clearly that the cutting edge radius develops differently for each regarded material and at different number of strokes. Therefore, it is of utmost importance to perform wear tests on different numbers of strokes under industrial conditions. With the knowledge gained, it will be possible to design optimized punches with lower costs and increased lifetime.