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Over the past few decades early self-regulation has been identified as foundational to positive learning and wellbeing trajectories. As a consequence, a wide range of approaches have been developed to capture children’s developmental progress in self-regulation. More recently, there has been increasing interest in ecologically valid measures of self-regulation, given questions about the extent to which self-regulation tasks with unfamiliar demands and situations reliably index children’s real-world self-regulation (e.g., ability to share, take turns, sustain attention, resist contrary impulses, overcome frustration, be increasingly self-directed). Little is known, however, about: (1) how these novel ecologically valid measures compare with measures from other approaches (e.g., task-based, educator-report); and (2) which yield reliable indicators of future outcomes and risk for young children. This study examined measures from prominent approaches to self-regulation assessment–a play-based observation measure of self-regulation designed to optimise ecological validity (PRSIST), a task-based measure (HTKS) and an adult-report measure (CBRS)–to determine: the degree of association between the indices generated by these highly divergent measurement approaches; how each predicts future academic school readiness; and whether thresholds could be ascertained to reliably discriminate children at risk of poor academic outcomes. It was hypothesised that indices would show significant but non-perfect associations, would each predict school readiness (with the ecologically valid measure yielding best predictive strength), and would contribute to longitudinal prediction of academic risk. Analyses of longitudinal data from 217 3-5-year-old Australian children indicated moderate to strong associations between the self-regulation indices from these different approaches. Start-of-year cognitive self-regulation indices–but not behavioural or emotional self-regulation indices–from each approach reliably predicted school readiness 7 months later, prior to commencing school. Only when combined into a composite score was a threshold with sufficient sensitivity and specificity for predicting school readiness risk created; yet this provided better prediction of true-negative than true-positive cases. Taken together, these results suggest the viability of ecologically valid approaches to self-regulation measurement and emphasise self-regulation as one of the important contributing factors to school readiness and academic risk.