A system and method are described for monitoring user location and activity over a period of time and intelligently scheduling content distributions to the user's mobile device. For example, one embodiment of a system for intelligently scheduling a content distribution to a mobile device comprises: a location database to store a plurality of different locations including event facilities and points of interest, the location database associating each of the different locations with a Global Positioning System (GPS) location or range of GPS locations; a data collection module for collecting user location data over a period of time, user location data specifying a user's mobile device's location throughout the period of time, the data collection module to store the user location data within a database; a predictive scheduler module to analyze the user location data over the period of time and responsively schedule content distributions to the user's mobile device based on the analysis of the user location data.