Summary: We propose Conditional Imputation GAN, an extended missing data imputation method based on Generative Adversarial Networks (GANs). The motivating use case is learning-to-rank, the cornerstone of modern search, recommendation system, and information retrieval applications. Empirical ranking datasets do not always follow standard Gaussian distributions or Missing Completely At Random (MCAR) mechanism, which are standard assumptions of classic missing data imputation methods. Our methodology provides a simple solution that offers compatible imputation guarantees while relaxing assumptions for missing mechanisms and sidesteps approximating intractable distributions to improve imputation quality. We prove that the optimal GAN imputation is achieved for Extended Missing At Random and Extended Always Missing At Random mechanisms, beyond the naive MCAR. Our method demonstrates the highest imputation quality on the open-source Microsoft Research Ranking Dataset and a synthetic ranking dataset compared to state-of-the-art benchmarks and across various feature distributions. Using a proprietary Amazon Search ranking dataset, we also demonstrate comparable ranking quality metrics for ranking models trained on GAN-imputed data compared to ground-truth data.