The article aims to study the distribution of residual stresses across the surface layer depth following the machining of test specimens (free orthogonal cutting and burnishing). The machining by cutting and burnishing of 45 steel specimens was carried out using a milling machine with numerical control under varying machining factors. For a comparative analysis, the processes were also modeled via the finite element method using identical experimental values of geometric parameters and machining modes. In order to obtain residual stress distributions across the surface layer depth, probe holes having depths of 0.5; 0.75; 1; 1.5; and 2 mm were drilled. By differentiating the displacement of specimen surface particles, measured using digital image correlation, radial strains around the probe holes were determined. Then, these values were used to determine the residual stress components for each probe hole, and the averaged values of each residual stress component were calculated using the calculation algorithm presented in this article. After burnishing the specimen with a force of 3400 N, the test value of the σx component within the depth range (from the surface) of 0.5–0.75 mm amounted to -250 MPa. Model and experimental distributions of residual stress tensor components across the surface layer depth were obtained following machining via two methods. The experimental values of residual stresses were found to have good convergence with each other and with model distributions at depths up to 1 mm from the machined surface at a drill diameter of 1.7 mm. The proposed approach provides a means to obtain the residual stress distribution across the surface layer depth by drilling probe holes of different depths and estimating radial strains on the specimen surface using the digital image correlation method.