In this study, we report the aromatic C─C bond cleavage of cyclopentadienide by transient imino(metallophosphino)silylenes through the reaction of silylene equivalents with CpCo(CO)2, enabling the transformation of cyclopentadienides into silicon-bridged homocyclopentadienides. The presence of homoaromaticity in these species is substantiated by NICS and ACID analyses.