Raman scattering technique was used to investigate the structural phase transformations and multiple phase generation of silicon induced by cyclic microindentations. Indentation cycles were performed on three different samples: monocrystalline, amorphous film, and on partially amorphous silicon generated by single point diamond turning. The results indicated that the formation of some pressure induced structural phases may be dependent upon the initial structural state of the materials surface: Several different structural phases were only observed in crystalline and partially amorphous Si after microindentation cycles. For completely amorphous Si, no phase formation was evidenced even after several cyclic indentations.