Methods and apparatus to monitor a multimedia presentation including multiple content windows are disclosed. An example method to monitor a media device providing a media presentation capable of including a plurality of content windows disclosed herein comprises obtaining a monitored image corresponding to the media presentation provided by the media device, determining a parameter value representative of at least one of a luminance or a chrominance of a region in the monitored image, a shape of the region representative of at least one of the plurality of content windows, and comparing the parameter value to a highlight threshold to determine whether a content window associated with a location of the region in the monitored image is highlighted.