Cobalt(II)-pyridinedicarboxamide-co-polydimethylsiloxane (Co-Py-PDMSs) and cobalt(II)-bipyridinedicarboxamide-co-polydimethylsiloxane (Co-Bipy-PDMSs) polymer-metal complexes were prepared by complexation between Py-PDMSs or Bipy-PDMSs ligands and cobalt(II); the metal content in these complexes varied from 0.09 to 2.41 wt %. The CoII binding patterns (the Co-NPy and Co-O coordination in Co-Py-PDMSs and Co-NBipy in Co-Bipy-PDMSs) were established by UV-vis and IR methods and by comparison with model CoII complexes exhibiting relevant O,N,O- and N,N-coordination environments, respectively. The mechanical properties of the polymer-metal complexes were controlled by the coordination of Py-PDMSs or Bipy-PDMSs to CoII at various metal-to-ligand molar ratios (1:(1-6)) and by the variation of the polydimethylsiloxane unit length (Mn: 850-900, 5000, or 25 »000 g·mol-1). Utilization of the chelated Py-PDMSs and Bipy-PDMSs polymer ligands, which are capable of tri- or bidentate binding of CoII, led to (2-4)-fold increases in tensile strength (up to 1.75 MPa) and much higher elongation at break ((2-3)-fold increase up to 2100%) compared with the previously reported CoII-based polymer-ligand systems featuring monodentate ligation entities. Changing the main-chain ligand from Py-PDMSs to Bipy-PDMSs led to an increase in tensile strength of (2-4)-fold in comparison with Py-PDMS and a lower hysteresis (4%). The room temperature self-healing efficiency was up to 96% for Co-Py-PDMSs and 40% for Co-Bipy-PDMSs, as measured for a polydimethylsiloxane unit with Mn = 25 »000 g·mol-1.