Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. Using a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed enabling to construct two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display broad scope and excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of post-catalytic modifications.