Learning-to-Rank is a branch of supervised machine learning that seeks to produce an ordering of a list of items such that the utility of the ranked list is maximized. Unlike most machine learning techniques, however, the objective cannot be directly optimized using gradient descent methods as it is either discontinuous or flat everywhere. As such, learning-to-rank methods often optimize a loss function that either is loosely related to or upper-bounds a ranking utility instead. A notable exception is the approximation framework originally proposed by Qin et al. that facilitates a more direct approach to ranking metric optimization. We revisit that framework almost a decade later in light of recent advances in neural networks and demonstrate its superiority empirically. Through this study, we hope to show that the ideas from that work are more relevant than ever and can lay the foundation of learning-to-rank research in the age of deep neural networks.