With the increased usage of Carbon Fiber Reinforced Plastics (CFRP) in the aircraft industry, there has been increased pressure to improve cutting tool life. Tungsten carbide tools were the first to be applied to CFRP materials. Poly Crystalline Diamond (PCD) tools also became an acceptable material to be used as a cutting tool material. In recent years, Chemical Vapor Deposition (CVD) diamond tools have become more popular as a cutting tool material for CFRP. This study compares these possible cutting tool materials in the drilling of CFRP. Wear is measured as well as hole quality. Life is determined by common industry standards with regard to fiber break out in a common CFRP material. An economic analysis is conducted in order to determine cost per hole.