The present disclosure describes an administration system which facilitates efficient setup, organization, and maintenance of tournaments, including league games. In particular, the administration system provides a user-friendly, intuitive and efficient-to-use interface for organizing tournaments and tournament brackets. The user interfaces and methods described provide tournament organizers and administrators with the ability to quickly and dynamically build custom tournament brackets of virtually any desired depth and configuration. The administration system, and in particular the tournament bracket management user interfaces, enable tournament administrators to focus on the task of building a custom tournament bracket structure quickly, while also automatically handling the minute logistics underlying the tournament such as when and where games are to be played.