The degree of oligomerization in the Wurtz-type coupling of 1,1,2,2-tetrachlorocyclooligosilanes was found to be controlled by the ring sizes of the cyclooligosilanes. The Wurtz-type coupling of 1,1,2,2-tetrachlorocyclotetrasilane, -cyclopentasilane, and -cyclohexasilane gave a tetramer, a trimer, and a dimer, respectively. These oligomers are the first examples of octasilacuneane, hexasilabenzvalene, and bicyclo[4.1.0]heptasil-1(6)-ene derivatives.