In this paper we present our 5-year-experience with a large-scale mentoring program for undergraduate medical students at the Ludwig Maximilians-Universität Munich (LMU). We implemented a two-tiered program with a peer-mentoring concept for preclinical students and a 1:1-mentoring concept for clinical students aided by a fully automated online-based matching algorithm. Approximately 20-30% of each student cohort participates in our voluntary mentoring program. Defining ideal program evaluation strategies, recruiting mentors from beyond the academic environment and accounting for the mentoring network reality remain challenging. We conclude that a two-tiered program is well accepted by students and faculty. In addition the online-based matching seems to be effective for large-scale mentoring programs.