This work aims to understand the influence of cutting parameters on the twist high-speed steel (HSS) drill bits wear when drilling C35 steel before and after quenching. An experimental investigation has been conducted using the planning experience methodology (L8) on C35 steel in the annealed and hardened states. The input parameters are cutting regime elements, cutting speed (Vc), feed rate (f), and drill diameter (D), while the output parameters are the tool wear related to its tool life. The most interesting phenomenon is the controversial effect of cutting speed when drilling C35 steel in hardened conditions. The drilling life increases with increasing cutting speed for different cutting regimes (1 to 8). In addition, the 20 mm diameter drill related to the high value of the depth of cut (f) has given better life before and after hardening, contrary to the literature on cutting tool life. The analysis of variance (ANOVA) has showed that the feed rate (f) is the most significant factor in the annealed state while it is the depth of cut (ap) in the hardened state. The correlation coefficients R2 determined by the ANOVA before, and after quenching, are very satisfactory, and testify the good adequacy of the proposed model.