In this paper, we investigate in detail the relationship between entropy and guesswork. The aim of the study is to lay the ground for future efficiency comparison of guessing strategies. After a short discussion of the two measures, and the differences between them, the formal definitions are given. Then, a redefinition of guesswork is made, since the measure is not completely accurate. The change is a minor modification in the last term of the sum expressing guesswork. Finally, two theorems are stated. The first states that the redefined guesswork is equal to the concept of cross entropy, and the second states, as a consequence of the first theorem, that the redefined guesswork is equal to the sum of the entropy and the relative entropy.