This paper presents results of a systematic – computer assisted – study focused on determining, and describing, from a mathematical point of view, the relationship between the drill point geometrical features and predicted performance measures as assessed by the cutting forces (thrust and torque) and cutting power when drilling a Type Bisalloy 360 steel work-piece material with general purpose twist (GPT) drills. The current study presents an innovative predictive strategy for eliminating the need of experimental testing when comparing drilling performance of GPT drills. It employs an advanced computer assisted model to analyse the rake angle distributions along the drill lips and the chisel edge regions when changing the six main individual drill point geometrical features (D, 2W, δO, ψ, ClO, and 2P) in the software input and looking at their effects on the generation of thrust, torque and power in drilling. It is expected that this sort of information may be used to assist in optimisation of the cutting performance of drills via advances through the modification of drill point geometrical features.