The effects of indenter/coating modulus mismatch on contact damage in bilayer systems composed of brittle coating layers on compliant polymeric underlayers is investigated. Convex specimens having curvature of 12 mm inner coating diameter are produced, and loaded using flat indenters of four different moduli. Glass plates of d = 1 mm thick are used as representative of the brittle coating, and soft epoxy filler is used as an underlayer. Specimens are loaded along the convex axis of symmetry. In this fashion the influence of indenter modulus on radial crack initiation and damage evolution is examined. Previous studies utilised hard spherical indenters of various sizes, and did not consider the effect of a compliant indenter on radial crack evolution and subsequent damage patterns. It is demonstrated that critical loads for initiation of radial cracks and subsequent damage patterns especially at specimen margins are sensitive to indenter modulus (indenter/coating modulus mismatch).