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Cognitive flexibility can be thought of as the ability to effectively adapt one's cognitive and behavioural strategies in response to changing task or environmental demands. To substantiate the common inference that self-report and neuropsychological tests of cognitive flexibility provide ‘different windows into the same room’, we undertook a systematic review and meta-analysis to determine whether self-report and neuropsychological tests of cognitive flexibility are related in healthy adults. Ten databases and relevant grey literature were searched from inception. The Preferred Reporting Items for Systematic Reviews and Meta-Analyses guidelines were adhered to. Twenty-one articles satisfied our inclusion criteria. A multi-level random-effects meta-analysis revealed no relationship (0.05, 95% CI = −0.00 to 0.10). Random-effects meta-analyses raised the possibility that the Cognitive Flexibility Scale and the Trail Making Test – part B (time) may be related (0.19, 95% CI = 0.06 to 0.31). We conclude that the relationship between self-report and neuropsychological tests of cognitive flexibility is not large enough to be considered convincing evidence for the two assessment approaches sharing construct validity. These results have clear implications for assessing and interpreting cognitive flexibility research and clinical practice Refereed/Peer-reviewed