Aspects of the invention provide systems and methods for facilitating a recurring series of distinct drawings (e.g., lottery, sweepstakes, raffles, etc.), for a prize or a variety of prizes (e.g., from one source or a variety of sources), over an extended period of time, or for an open-ended period of time. In addition, a user can enter the recurring series of drawings through a single registration (e.g., entry into a drawing database). The entrant will be continuously entered into the series of recurring drawings until the entrant is removed from the database, e.g., opts out of the system. In one embodiment, preferences and attributes can be determined for each entrant and these preferences and attributes can be used to enter the entrant into a customized series of recurring drawings.