A system and method to facilitate real-time matching of content to advertising information in a network are described. A request for advertising information is received over a network, the advertising information to be displayed for a user entity in association with content information within a web page requested by the user entity, the request containing the content information, a web page identifier, and additional data associated with the web page. The content information is further analyzed in real-time to construct a page summary of the web page. The web page identifier and the additional data are further analyzed in real-time to extract at least one keyword relevant to the content information. Finally, the advertising information is determined in real-time based on the page summary and the extracted keywords.