The current study presents three calibration approaches for the hole-drilling method (HDM). A total of 72 finite element models and 144 simulations were established to calibrate the measurements of the strain sensors. The first approach assumed the stresses acted on the boundaries of the drilled hole and thus analyzed the surrounding displacements field. The second analysis considered the loads on the outer surfaces of the specimen while measuring the strains’ differences between the model with and without the drilled hole. The third approach was more comprehensive as it considered the mechanical and thermal effects of the drilling operations. The proposed approaches were applied to two different materials (AISI 1045 and CFRP). The steel specimens were machined using a CNC lathe while the composite laminates were manufactured using the robotic fiber placement (RFP) process. Subsequently, the residual stresses (RSs) were measured using the HDM. The obtained data were compared with X-ray diffraction measurements for validation. The results showed better estimation of the RSs when utilizing the third approach and clear underestimation of the stresses using the second approach. A divergence in RSs values between the three approaches was also detected when measuring the stresses in the internal layers of the composite laminates.