A series of syndiospecific C-1-symmetric ansa-metallocenes ([Me2X(Cp)(2-R-1-3-R-2-Ind)]ZrCl2, X = C, Si; R-1 = H, Me; R-2 = Me, Et, CH2SiMe3) have been synthesized, and their catalytic behavior in the polymerization of propylene has been studied. Upon activation with MAO, these carbon- or silicon-bridged cyclopentadienyl/indenyl systems afford polypropylene with various degrees of syndiotacticity ([rrrr] = 28-66%), as a function of the substituent size, substitution pattern, and bridging moiety. The silicon-bridged systems produced PP samples of higher molecular weight, lower syndiotacticities, and comparable productivities with respect to their carbon-bridged analogues. Statistical modeling of the experimental pentad distributions suggests that site epimerization is the major cause of stereoerrors within both sets, while a decreased site stereo specificity can be implied for the silicon-bridged systems.