As readily available and abundant industrial feedstocks, alkenes have emerged as versatile platform for constructing value-added targets. Transition metal-catalyzed dicarbofunctionalizations reactions forge two carbon-carbon bonds in one step with construction of two vicinal saturated carbon centers, providing profound synthetic potential in organic synthesis and pharmaceutical chemistry. In particular, nickel-catalyzed reductive dicarbofunctionalization of alkenes has witnessed remarkable progress in recent years. Compared to conventional redox-neutral dicarbofunctionalization strategy, reductive variant offers significant advantages, such as no use of pre-formed organometallic reagents, operational simplicity and mild reaction conditions. This review summarizes developments of nickel-catalyzed reductive dicarbofunctionalization of alkenes to forge diverse carbon-carbon bonds in the absence of stoichiometric carbon nucleophiles. The mechanistic considerations are comprehensively discussed, including two-electron migratory insertion and the single-electron radical addition pathways. Furthermore, we provide critical insights into future directions and potential challenges in this area, highlighting opportunities for further methodology development and applications for nickel-catalyzed reductive dicarbofunctionalization of alkenes.