Tie-point matching of off-track stereo images is a very challenging task, which can impact bias compensation and digital surface model (DSM) generation. Compared to in-track stereo images, off-track stereo images are more complex primarily due to the radiometric differences caused by sun illumination, sensor responses, atmospheric conditions, and seasonal land cover variations, and secondly due to the longer baseline and larger intersection angle. These challenges significantly limit the use of the vast number of images in satellite archives for automated geometric processing and mapping. Recent advances in deep learning (DL) based matching show promising results against images with diverse illuminations, viewing angles and scales through learning examples. This paper evaluates the potentials of addressing the tie point matching problems in off-track satellite stereo images. Specifically, we focus on stereo pairs that failed or underperformed in classic matching algorithms (i.e., SIFT (scale invariant feature transform)), and evaluate the DL-based tie points matchers by its resulting geometric accuracy in relative orientation, and the generated DSM. The experiments are carried out using 40 off-track satellite stereo pairs from four different regions around the world. We conclude that DL-based methods provide a significant higher success rate in matching challenging multi-temporal stereo pairs, even if their matching accuracy is slightly lower than classic algorithms.