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We study a relaxation of the problem of coupling probability distributions — a list of samples is generated from one distribution and an *accept* is declared if any one of these samples is identical to the sample generated from the other distribution. We propose a novel method for generating samples, which extends the Gumbel-max sampling suggested in Daliri et al. (2025) for coupling probability distributions. We also establish a corresponding lower bound on the acceptance probability, which we call the \emph{list matching lemma}. We next discuss two applications of our setup. First, we develop a new mechanism for multi-draft speculative sampling that is simple to implement and achieves performance competitive with baselines such as SpecTr and SpecInfer across a range of language tasks. Our method also guarantees a certain degree of *drafter invariance* with respect to the output tokens which is not supported by existing schemes. We also provide a theoretical lower bound on the token level acceptance probability. As our second application, we consider distributed lossy compression with side information in a setting where a source sample is compressed and available to multiple decoders, each with independent side information. We propose a compression technique that is based on our generalization of Gumbel-max sampling and show that it provides significant gains in experiments involving synthetic Gaussian sources and the MNIST image dataset.