Abstract: An advertisement player is described that embeds on a web page having a video player, which is hosted on a first server. The advertisement player is configured to make a call to and send information associated with a video file about to be played on the web page across a network to a contextual engine hosted on a second server. The contextual engine analyses the content of the video file to be played on the video player and content of two or more advertisements from two or more advertisement networks and sends back one or more advertisements to display with the video file as the video player plays the video file on the web page. The contextual engine pairs the one or more advertisements with the video file based on at least a best match of relevance of the one or more advertisements to content in the video file.