We consider the design of computationally efficient online learning algorithms in an adversarial setting in which the learner has access to an offline optimization oracle. We present an algorithm called Generalized Follow-the-Perturbed-Leader and provide conditions under which it is oracle-efficient while achieving vanishing regret. Our algorithm generalizes the Follow-the-Perturbed-Leader (FTPL) approach of Kalai and Vempala [32] in which the action with the highest randomly perturbed historical performance is chosen on each round. FTPL is inefficient when the number of actions is exponential in the parameters of interest. Our algorithm creates more compact perturbations by augmenting the observed history with randomly generated synthetic history, and choosing the action with the (near) best performance on this augmented history. As we show, when certain structural properties hold, the augmented history is of polynomial size even when the learner's action space is exponential, yielding oracle-efficient learning. Our results make significant progress on an open problem raised by Hazan and Koren [27], who showed that oracle-efficient algorithms do not exist in general [26] and asked whether one can identify properties under which oracle-efficient online learning may be possible.Our second main contribution is the introduction of a new adversarial online auction-design framework for revenue maximization and the application of our oracle-efficient learning results to the adaptive design of auctions. In our framework, a seller repeatedly sells an item or set of items to a population of buyers by adaptively selecting auctions from a fixed target class. The goal of the seller is to leverage historical bid data to pick an auction on each iteration in such a way that the seller's overall revenue compares favorably with the revenue he would have obtained using the best auction from the class in hindsight. Since this is a specific case of adversarial online learning, we can apply our framework and provide new oracle-efficient learning results for: (1) Vickrey-Clarkes-Groves (VCG) auctions with bidder-specific reserves in single-parameter settings, (2) envy-free item pricing in multi-item auctions, and (3) the level auctions of Morgenstern and Roughgarden [37] for single-item settings. The last result leads to an approximation of the overall optimal Myerson auction when bidders' valuations are drawn according to a fast-mixing Markov process, extending prior work that only gave such guarantees for the i.i.d. setting.Finally, we derive various extensions, including: (1) oracle-efficient algorithms for the contextual learning setting in which the learner has access to side information (such as bidder demographics), (2) learning with approximate oracles such as those based on Maximal-in-Range algorithms, and (3) noregret bidding in simultaneous auctions, resolving an open problem of Daskalakis and Syrgkanis [13].