The interactions between a hemi-implant head and the native glenoid cavity are determinant in the efficiency and longevity of the medical strategy. The glenoid tissues harvested from three clinical cases who underwent different types of shoulder hemi-arthroplasty were investigated. A first case with a cobaltchrome (CoCr) head presented a loose and multi-layered fibrocartilaginous tissue with CoCr particles and areas of inflammation. The bone marrow was hypercellular and fibrous, highlighting the inflammatory state of the joint. The second case with a pyrocarbon (PyC) head presented a glenoid membrane made of articular cartilage and fibrocellular tissue with collagen II expression. The third case with a PyC head and subchondral microdrills presented the tissue with the best quality. The glenoid membrane was mainly composed of articular cartilaginous like tissue and the bone marrow presented a normal morphology, with some expression of collagen II on the vascular walls. A lipidomic analysis showed that the PyC had a better capacity to adsorbed a layer of lipids on its surface compared to the CoCr. The amount of lipids was enhanced in the case of subchondral microdrills, probably due to the liberation of the bone marrow lipids. As it is known for the healthy cartilage, a lipids layer improves the biomechanical interaction occurring at the implant-glenoid cavity interface in favour of decreased frictional forces and an enhanced joint integrity. Despite the limitations of the current study, these results strongly support for further investigations of the PyC-glenoid tissues interactions.