Systems and methods are disclosed herein for managing recorded media assets through advertisement insertion. A media guidance application may record and store media assets for later viewing by a user. To help ensure that the user views older recordings first, the media guidance application may insert advertisements into media assets which are part of a program series where there are older recorded media assets of the same program series that have not yet been watched by the user. The media guidance application may determine that multiple media assets are part of the same program series, and which of the media assets was recorded latest. The media guidance application may then select a play position within the later-recorded media asset and insert an advertisement at the selected play position.