Through the use of N-[2′-ferrocenylformamido-ethyl]-cis-5-norbornene-exo-2,3-dicarboximide (NFc) and N-[2′adamantylformamido-ethyl]-cis-5-norbornene-exo-2,3-dicarboximide (NAd), we report the fabrication of two novel supramolecular norbornene monomers, NFc@β-CD and NAd@β-CD, through β-cyclodextrin (β-CD)/ferrrocene(Fc)-and β-CD/adamantane (Ad)-based host-guest complexation. The formation and structure of the two monomers were verified by various techniques, such as 1 H and 13 C NMR, 2D NOESY, IR and UV-vis spectroscopic methods. The ROMP (ring-opening metathesis polymerization) feasibility of the two supramolecular monomers was further confirmed by the successful preparation of two homopolymers (P(NFc@β-CD) and P(NAd@β-CD)) and two diblock copolymers (PNFc-b-P(NAd@β-CD) and P(NFc@β-CD)-b-P(NAd@β-CD)). The prepared polymers were adequately analyzed using 1 H and 13 C NMR, IR, UV-vis, end-group analysis and GPC methods. Based on the obtained results, we believe that (1) both supramolecular monomers exhibited "living" and "controlled" ROMP reactions; (2) the β-CD/Fc and β-CD/Ad inclusion complexes were not disassembled during the ROMP reactions of the two supramolecular monomers; and (3) the functional groups of β-CD had a negligible effect on the catalytic activity of the third-generation Grubbs' catalyst. In short, this work indicated that the direct ROMP of β-CD-containing supramolecular monomers was a feasible route for preparing supramolecular polynorbornene-based homopolymers and copolymers, and this route is expected to have great potential for the preparation of various supramolecular polynorbornenes and functional materials.