Polysubstituted cyclohexenes bearing 1,3 (meta) substitution patterns are challenging to access using the Diels-Alder reaction (the ortho-para rule). Here, we report a cobalt-catalyzed reductive [5 + 1]-cycloaddition between a vinylcyclopropane and a vinylidene to provide methylenecyclohexenes bearing all-meta relationships. Vinylidene equivalents are generated from 1,1-dichloroalkenes using Zn as a stoichiometric reductant. Experimental observations are consistent with a mechanism involving a cobalta clobutane formed from a [2 + 2]-cycloaddition between a cobalt vinylidene and a vinylcyclopropane.