The predictions of question answering (QA) systems are typically evaluated against manually annotated finite sets of one or more answers. This leads to a coverage limitation that results in underestimating the true performance of systems, and is typically addressed by extending over exact match (EM) with predefined rules or with the token-level F1 measure.In this paper, we present the first systematic conceptual and data-driven analysis to examine the shortcomings of token-level equivalence measures.To this end, we define the asymmetric notion of answer equivalence (AE), accepting answers that are equivalent to or improve over the reference, and publish over 23k human judgements for candidates produced by multiple QA systems on SQuAD.Through a careful analysis of this data, we reveal and quantify several concrete limitations of the F1 measure, such as a false impression of graduality, or missing dependence on the question.Since collecting AE annotations for each evaluated model is expensive, we learn a BERT matching (BEM) measure to approximate this task. Being a simpler task than QA, we find BEM to provide significantly better AE approximations than F1, and to more accurately reflect the performance of systems.Finally, we demonstrate the practical utility of AE and BEM on the concrete application of minimal accurate prediction sets, reducing the number of required answers by up to X2.6.