Ground Control Points (GCP), automatically extracted from Synthetic Aperture Radar (SAR) images through 3D stereo analysis, can be effectively exploited for an automatic orthorectification of optical imagery if they can be robustly located in the basic optical images. The present study outlines a SAR/Optical cross-matching procedure that allows a robust alignment of radar and optical images, and consequently to derive automatically the corresponding sub-pixel position of the GCPs in the optical image in input, expressed as fractional pixel/line image coordinates. The cross-matching in performed in two subsequent steps, in order to gradually gather a better precision. The first step is based on the Mutual Information (MI) maximization between optical and SAR chips while the last one uses the Normalized Cross-Correlation as similarity metric. This work outlines the designed algorithmic solution and discusses the results derived over the urban area of Pisa (Italy), where more than ten COSMO-SkyMed Enhanced Spotlight stereo images with different beams and passes are available. The experimental analysis involves different satellite images, in order to evaluate the performances of the algorithm w.r.t. the optical spatial resolution. An assessment of the performances of the algorithm has been carried out, and errors are computed by measuring the distance between the GCP pixel/line position in the optical image, automatically estimated by the tool, and the “true” position of the GCP, visually identified by an expert user in the optical images.