A system and method to facilitate 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. Advertising information related to one or more themes of the content information on the web page is further determined, the themes representing subject matter contextually related to the content information. Advertisements are further selected from the advertising information based on keywords and metadata stored within the web page and based on a set of predetermined parameters stored within the data storage module. The selected advertisements are further ranked to obtain a ranked list of advertisements. The ranked list of advertisements is subsequently optimized based on feedback data to obtain a list of optimized advertisements to be displayed for the user entity on the requested web page.