Multi-walled carbon nanotubes (MCNTs)-enhanced glass fiber composite (GFC) laminates are among the most promising materials for fulfilling various structural and non-structural requirements. They have also shown exceptional functional applications as excellent electrical and thermal conductors, as well as electromagnetic interference shielding materials. The present work primarily focuses on developing regression models for the drilling process of 0.3 wt% MCNTs-GFC laminates. For experimentation, three different coated drills—carbide, TiCN-coated, and TiAlN-coated—are used under both dry and chilled air cutting environments. The lowest thrust force, torque, and delamination factor were observed at a feed rate of 10 mm/min and a speed of 1500 RPM using a TiCN-coated drill in a chilled air environment. Regression analysis reveals that feed rate significantly influences thrust force, as justified by the R² value, which is above 90% for the selected cutting conditions. The corresponding t and F statistics values indicate the statistical significance of the relevant explanatory factors. The efficiency of the developed models is further validated by considering the Akaike Information Criterion (AIC) and Bayesian Information Criterion (BIC) values, which are 136.9 and 144.7, respectively. These values indicate a good regression fit and likelihood of the models for data prediction. Additionally, there is a strong correlation (coefficient > 0.85) between thrust force and delamination factor under the selected cutting environments. Concurrently, the developed regression models are simulated and evaluated for random experiments (Nos. 87, 125, 187, 243, 244, and 399), and the predicted responses closely match the experimental values.