The reaction of [(eta(5)-C(5)H(5))Cu(CNPh)] with phenyl-isocyanide results in an unprecedented double migratory insertion into two sp(2) C-H bonds of a eta(5)-coordinated cyclopentadienyl group, and formation of the 6-aminofulvene-2-aldimine complexes [(CNPh)Cu{kappa(2)-N,N-C(5)H(3)-1,2-(CHNPh)(2)}] and [(CNPh)(2)Cu{kappa(2)-N,N-C(5)H(3)-1,2-(CHNPh)(2)}], respectively, both of which have been structurally characterised.