Asymmetric anionic polymerization of a prochiral quinone methide monomer, 7-cyano-7-ethoxycarbonyl-1,4- benzoquinone methide (1), was examined using two chiral anionic initiators, lithium 4-isopropylphenoxide ((PrPhOLi)-Pr-i)/(-)-sparteine((-)-Sp) and (PrPhOLi)-Pr-i/(S)-(-)-2,2'-isopropylidenebis(4-pheny1-2oxazoline) ((-)-PhBox) initiators, in a mixture solution of dichloromethane/toluene (30/70 in vol %), and optical activities of the resulting polymers and oligomers (1-mer and 2-mer) were investigated in detail. On asymmetric anionic polymerization of 1 with (PrPhOLi)-Pr-i/(-)-Sp initiator, stereoselectivity was quite low on both initiation and propagation reactions, while in the case of (PrPhOLi)-Pr-i(-)-Ph Box initiator, stereoselectivity was quite low on the initiation reaction, but the propagation reaction proceeded stereoselectively, resulting in an optically active polymer of 1 (poly(1)) with a large positive specific rotation.