Abstract Group 9 transition metals with a cyclopentadienyl-type ligand are highly reactive catalysts for directed C–H functionalization reactions. In this review, we summarize our recent work on the development of enantioselective C–H functionalization reactions using achiral Rh(III) or Co(III) catalysts in combination with an external chiral source such as chiral sulfonates, a Lewis base, or carboxylic acids.