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Long-term baseline data that allow tracking how predator–prey interactions have responded to intensifying human impacts are often lacking. Here, we assess temporal changes in benthic community composition and interactions between drilling predatory gastropods and their molluscan prey using the Holocene fossil record of the shallow northern Adriatic Sea, which is characterized by a long history of human transformation. Molluscan assemblages differ between the Isonzo and Po prodelta, but both show consistent temporal trends in the abundance of dominant species. Samples of mollusc prey collected at high stratigraphic resolution indicate that drilling frequencies have drastically declined in the Po prodelta since the mid-twentieth century, while a weaker trend in the more condensed sediments of the Isonzo prodelta is not statistically significant. The decrease in drilling predation intensity and the community turnover are linked to the loss of predatory gastropods and the increased relative abundance of less-preferred prey during the most recent decades. Our results align with data showing the substantial depletion of marine resources at higher trophic levels in the region and indicate that the strong simplification of the food web initiated in the late nineteenth century accelerated further since the mid-twentieth century. [ABSTRACT FROM AUTHOR]