Media device systems and methods synchronize video content with audio content presented by a plurality of wireless audio headsets. In an exemplary embodiment, a first time delay corresponds to a first duration of time between communication of the audio content from the media device and presentation of the audio content by a first wireless audio headset. A second time delay corresponds to a second duration of time between communication of the audio content from the media device and presentation of the audio content by a second wireless audio headset, wherein the first time delay is greater than the second time delay. Video content communicated to a display is delayed by the first time delay. Audio content communicated to the second wireless audio headset is delayed by a time delay difference between the first time delay and the second time delay.