The goal of this paper is to share our experience in designing and organizing educational competitions with anonymous and (near) real-time leaderboards in both academic and industrial settings. While such competitions serve as a great educational tool and provide participants with hands-on experience, they require significant planning, technical setup, and administration from organizers. In this paper, we first outline several important areas including team registration, data access, submission systems, rules and conditions that organizers should consider when planning such events. We then present a high-level system design that can support (near) real-time evaluation of submissions to power anonymous leaderboards and provide immediate feedback for participants. Finally, we share our experience applying this abstract system in academic and industrial settings. We hope the set of guidelines and the high-level system design proposed here help others in their organization of similar educational events.