Polymer‐metal complexes (PMCs) based on poly(2,2′‐bipyridine‐4,4′‐dicarboxamide‐co‐polydimethylsiloxanes) with cyclometalated di(2‐phenylpyridinato‐C2,N')iridium(III) fragments and cross‐linked by Zn2+ (Zn[Ir]‐BipyPDMSs) or Ir3+ (Ir[Ir]‐BipyPDMSs) represent flexible, stretchable, phosphorescent, and self‐healing molecular oxygen sensors. PMCs provide strong phosphorescence at λem = 595–605 nm. Zn[Ir]‐BipyPDMS with PDMS chain length of Mn = 5000 has the highest quantum yield of 9.3% and is a molecular oxygen sensor at different O2 concentrations (0–100 vol%) compared to Ir[Ir]‐BipyPDMSs. A Stern−Volmer constant is determined for Zn[Ir]‐BipyPDMS as KSV = 0.014%−1, which is similar to the reported oxygen‐sensitive iridium(III) complexes. All synthesized PMCs exhibit high elongation at break (up to 1100%) and self‐healing efficiency (up to 99%).