Alkene hydrosilylation is amongst the largest industrial homogenous catalysis processes. Cobalt catalysis offers a sustainable alternative to commonly used platinum catalysts to achieve this transformation. Using two bisiminopyridine cobalt(II) catalysts the regiodivergent hydrosilylation of alkenes has been developed. Variation of pre-catalyst activator and ligand substituents were investigated to enable the controlled, regiodivergent hydrosilylation of both aryl- and alkyl-substituted alkenes with phenylsilane. In contrast to other regiodivergence strategies, excellent regioselectivity for either isomer was achieved using the same ligand class but differing by a single methyl group (ethyl vs isopropyl).