When drilling Carbon Fibre-Reinforced Plastic (CFRP) materials, achieving acceptable hole quality is challenging while balancing productivity and tool wear. Numerical models are important tools for the optimization of drilling CFRP materials in terms of material removal rate and hole quality. In this research, a macro-Finite Element (FE) model was developed to accurately predict the effect of drill tip geometry on hole entry and exit quality. The macro-mechanical material model was developed treating the Fiber-Reinforced Plastic (FRP) as an Equivalent Homogeneous Material (EHM). To reduce computational time, a numerical analysis was performed to investigate the influence of mass scaling, bulk viscosity, friction, strain rate strengthening, and cohesive surface modelling. A consideration must be made to minimize the dynamic effects in the FE prediction. The experimental work was carried out to investigate the effect of drill tip geometry on drilling forces and hole quality and to validate the FE results. The geometry of the drills used were either double-point angle or a “candle-stick” profile. The 3D drilling model accurately predicts the thrust force and hole quality generated by the two different drills. The results highlight the improvement in predicted results with the inclusion of cohesive surface modelling. The force signature profiles between the simulated and experimental results were similar. Furthermore, the difference between the predicted thrust force and those measured were less than 9%. When drilling with a double-angle drill tip, the inter-ply damage was reduced. This trend was observed in FE prediction.