A method of transferring data and a method of transferring contents are provided. In the method of transferring data in a data interoperable environment, a secure authenticated channel is established with a receiving entity corresponding to receiver information included in a received control message, when the control message is received from a control entity, a plurality of data designated by the control entity are transmitted to the receiving entity through the established secure authenticated channel, and an event message for representing a transmission status of the transmitted data is transmitted to the control entity. Accordingly, it is possible to transmit the plurality of data through a single transmission session and provide a transmission status of each data through an event.