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Deep Neural Network (DNN) classifiers are vulnerable to adversarial attack, where an imperceptible perturbation could result in misclassification. However, the vulnerability of DNN-based image ranking systems remains under-explored. In this paper, we propose two attacks against deep ranking systems, i.e., Candidate Attack and Query Attack, that can raise or lower the rank of chosen candidates by adversarial perturbations. Specifically, the expected ranking order is first represented as a set of inequalities, and then a triplet-like objective function is designed to obtain the optimal perturbation. Conversely, a defense method is also proposed to improve the ranking system robustness, which can mitigate all the proposed attacks simultaneously. Our adversarial ranking attacks and defense are evaluated on datasets including MNIST, Fashion-MNIST, and Stanford-Online-Products. Experimental results demonstrate that a typical deep ranking system can be effectively compromised by our attacks. Meanwhile, the system robustness can be moderately improved with our defense. Furthermore, the transferable and universal properties of our adversary illustrate the possibility of realistic black-box attack.