In a series of recent papers, Randall and Foulis have developed a generalized theory of probability (operational statistics) which is based on the notion of a physical operation. They have shown that the quantum logic description of quantum mechanics can be naturally imbedded into this generalized theory of probability. In this paper we shall investigate the role of entropy (in the sense of Shannon's theory of information) in operational statistics. We shall find that there are several related entropy concepts in operational statistics. We shall examine the relationships between these different entropy concepts and examine their implications for the foundations of quantum theory. We shall also examine the extension of the Jaynes inference scheme to the operational statistics formalism, and apply the latter to the case of quantum statistical mechanics.