The chemoenzymatic synthesis of new side-chain polyrotaxanes (6) bearing non-covalently attached cyclodextrins is described. Starting from 11-methacryloylaminoundecanoic acid, up to 8 units of 12-hydroxylauric acid were condensed in the presence of a lipase from Candida antarctica. They were copolymerized with methyl methacrylate to comb-like polymers (4) bearing free carboxylic groups at the end of the oligoester side chains. These free carboxylic groups were then condensed chemically with a nucleophilic barrier group, N-(4-aminobutanoyl)-4-triphenylmethylaniline (5), in the presence of dimethylated beta-cyclodextrin, yielding new polyrotaxanes that contain statistically more than 1 ring component per side chain.