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Facilitated by the supramolecular synthons of carboxylic acids and amides through cooperative hydrogen‐bonding and arene–perfluoroarene interactions, the azide–alkyne cycloaddition reaction between two different molecules in a cocrystal was achieved. This reaction could be accelerated by pressure using a common hydraulic press equipment with excellent regioselectivity to yield 1,4‐triazole products. The absence of decarboxylation side reactions in the products in the solid state demonstrated that this strategy can provide a green synthetic route for products not directly accessible by traditional syntheses in solution. [ABSTRACT FROM AUTHOR]