Tool wear and cutting parameters have a significant effect on the surface layer properties in milling. Since the relation between tool wear, cutting parameters, and surface layer properties is mostly unknown, the latter cannot be controlled during production and may vary from part to part as tool wear progresses. To account for this uncertainty and to prevent premature failure, components often need to be oversized or surface layer properties need to be adjusted in subsequent manufacturing processes. Several approaches have been made to obtain models that predict the surface layer properties induced by manufacturing processes. However, those approaches need to be calibrated with a considerable number of experimental trials. As trials are time-consuming and surface layer measurements are laborious, no industrial applications have been realized. Complex models have one major drawback. They have to be re-parameterized as soon as process characteristics change. Therefore, manual experimental parameterization does not appear to be a feasible approach for industrial application. A highly automated approach for the machine learning of the relation between tool wear, cutting parameters and surface layer properties is presented in this paper. The amount of obtained measurement data allows a fundamental analysis of the approach, which paves the way for further developments.