A system and method for automatically enrolling users of a website or other network-based service in sweepstakes. A user of 4 user computer system connects to a host computer system hosting a website or other network-based service and is awarded points for accessing features of the website or service. The points are displayed in real-time on the user's computer and transmitted to a database server, which maintains the user's point totals. The user is then automatically given a number of entries in a sweepstakes based on the number of points he or she has been awarded. Users may also be awarded points for accessing features of websites or services of third-party host computer systems.