Saturated stereogenic centers containing Csp3-Csp3 bonds are comprise major portion of organic molecules. Over the past decades, transition-metal-catalyzed asymmetric Csp3-Csp3 cross-coupling has been evolved into an efficient strategy for constructing such stereogenic centers. However, reaction modes to build asymmetric Csp3-Csp3 bonds remain very limited. Herein, a nickel-catalyzed asymmetric cross-hydrodimerization of distinct alkenes to enable the construction of asymmetric alkyl-alkyl bonds has been developed. In this reaction mode, N-acyl enamines (enamides) and unactivated alkenes undergo oxidative asymmetric cross-hydrodimerization with excellent levels of chemo- and head-to-tail regioselectivity to give enantioenriched N-acyl α-branched amines by forging the Csp3-Csp3 bond with the control of enantioselectivity. The presence of both reducing and oxidizing reagents in the reaction allows for the use of alkenes as sole precursors to forge enantioselective Csp3-Csp3 bonds, representing a new reaction mode for asymmetric alkyl-alkyl cross-coupling. The asymmetric cross-hydrodimerization of distinct alkenes provides a new strategy for constructing saturated stereogenic centers containing Csp3-Csp3 bonds.