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The present study evaluated the effect of maturity stage on the chemical composition of cardoon bracts. Plant material was collected in Greece at eight different maturation stages (C1–C8) and the chemical composition was analyzed in regard to lipidic fraction and the content in fatty acids, tocopherols, organic acids, and free sugars. Samples of late maturity (C6–C8) revealed the lowest lipidic content, while a total of 29 fatty acids was identified in all the samples, with palmitic, stearic, oleic, and eicosatrienoic acids present in the highest levels depending on harvesting time. Immature (C1) and mature (C8) bracts were more abundant in saturated fatty acids (SFA) than bracts of medium-to-late maturity (C5, C6), where the monounsaturated fatty acids (MUFA) were the prevalent class. The α- and γ-tocopherols were the only identified isoforms of vitamin E, while the highest content was observed in sample C8 (199 µg/100 g dry weight (dw). The detected organic acids were oxalic, quinic, malic, citric, and fumaric acids, while fructose, glucose, sucrose, trehalose, and raffinose were the main detected sugars. The results of the present study allowed us to reveal the effect of maturity stage on cardoon bracts chemical composition and further valorize this byproduct by improving its bioactive compounds content.