<p>Constructing ubiquitous bridged bicyclic scaffolds from simple aliphatic feedstocks via multiple C(<i>sp</i>³)–H functionalizations is a significant challenge in organic synthesis, demanding powerful catalysts capable of precise selectivity control. Here we demonstrate a catalytic system that enables abundant cyclic carboxylic acids to couple with dienophiles in a formal Diels–Alder manner with exclusive regioselectivity, forging bridged bicyclic scaffolds. Mechanistic studies revealed that the pyridine–pyridone ligand plays a crucial role in the β,γ-dehydrogenation of cyclic carboxylic acids, concerted decarboxylation process and subsequent regioselective β-hydride elimination through precise control of the electronic distribution of palladium and cyclic carboxylic acids and the steric interactions between them. Dienes generated in situ are rapidly intercepted by a variety of dienophiles, furnishing the bridged bicyclic motifs with exclusive endoselectivity. Notably, β-, γ- and δ-methylene C(<i>sp</i>³)–H bonds are functionalized with exclusive regioselectivity controlled by one catalyst.</p><p></p>