We study information leakage through \emph{guesswork}, the minimum expected number of guesses required to guess a random variable. In particular, we define \emph{maximal guesswork leakage} as the multiplicative decrease, upon observing $Y$, of the guesswork of a randomized function of $X$, maximized over all such randomized functions. We also study a pointwise form of the leakage which captures the leakage due to the release of a single realization of $Y$. We also study these two notions of leakage with oblivious (or memoryless) guessing. We obtain closed-form expressions for all these leakage measures, with the exception of one. Specifically, we are able to obtain closed-form expression for maximal guesswork leakage for the binary erasure source only; deriving expressions for arbitrary sources appears challenging. Some of the consequences of our results are -- a connection between guesswork and differential privacy and a new operational interpretation to maximal $\alpha$-leakage in terms of guesswork.