Reaction of the donor-stabilized silylene 1 with [Cr(CO)6], [Mo(CO)6], [W(CO)6], or [Fe(CO)5] leads to the formation of the transition-metal silylene complexes 2−5, which contain five-coordinate silicon(II) moieties with Si−M bonds (M = Cr, Mo, W, Fe). These compounds were characterized by NMR spectroscopic studies in the solid state and in solution and by crystal structure analyses. According to computational studies, the Si−M bonds are best described as single bonds.