While 1,2-regioselective difunctionalizations of alkenes are well developed, their migratory difunctionalization of alkenes remains comparatively under-researched. Herein, we report a nickel-catalyzed, divergent, solvent-controlled 1,1- or 1,3-regioselective benzylboration of allylbenzenes, that provides efficient access to primary and secondary alkyl boronates. The mild reaction conditions of these transformations allow good regioselectivity and wide functional group tolerance.