Methods and apparatus to monitor a media presentation are disclosed. An example apparatus includes a housing defining a sleeve dimensioned to receive a monitoring device, the monitoring device to monitor the media presentation. The example apparatus includes a receiver carried by the housing to receive a first modulated audio signal from a media device via a wireless data connection using a wireless communication protocol, the first modulated audio signal associated with the media presentation, the receiver to output a baseband audio signal corresponding to the first modulated audio signal. The example apparatus includes a speaker carried by the housing to emit the baseband audio signal for receipt by the monitoring device within the sleeve. The example apparatus further includes a transmitter carried by the housing to modulate the baseband audio signal to form a second modulated audio signal, the transmitter to transmit the second modulated audio signal to wireless headphones using the wireless communication protocol.