Fiber-reinforced plastic is one of the top priorities lightweight materials with excellent mechanical properties for the aerospace industries in recent years. However, it is difficult to machine despite having unique properties due to its non-homogeneous and abrasive nature in alternate fiber and matrix layers. Thus, it is found to be a challenging task to drill hole on such hard-to-machine materials, which is highly essential for the development of most of the engineering structural components. The present work addresses various drilling-induced defects such as delamination, circularity error, and roughness variations in the hole surface during drilling of quasi-isotropic cross-fiber oriented bi-directional woven-type carbon fiber reinforced plastic laminate using a full factorial design of experiments for different drill geometry. The response surface methodology was considered for the regression model development, which was found to be highly significant. The machining forces with associated torque have also been acquired during drilling, which was divided and further analyzed in time domain to correlate with drilling flaws. The drilling-induced delamination was found to be higher at a high feed rate using a higher drill point angle due to substantial thrust force generation at the initial stages in the drilling cycle. However, the internal surface finish with associated circularity error was reduced for higher spindle speed with less feed rate using a low drill point angle because of low torque fluctuation at the final drilling phases. The axial thrust force was found to be a prime indicator of drilled hole surface delamination, whereas drilling torque precisely indicated internal surface roughness as well as circularity error. The global root mean square, along with a local peak of thrust and torque, both were highly essential to completely characterize the drilled hole quality.