Trochleoplasty is an established and accepted technique for the treatment of patellar instability because of a missing trochlear groove. In this technique, a flap of cartilage over the trochlea is carefully removed and a new trochlear groove is created in the underlying bone before the cartilaginous flap is reattached with sutures. The mid-term clinical and radiological results of this operation are promising but no information about the viability of the reattached cartilage has been reported. To evaluate cartilage viability and quality after trochleoplasty and to verify the healing process, two osteochondral biopsies were harvested from three patients 6, 8, and 9 months after trochleoplasty. One cylinder was evaluated histologically to assess cartilage, calcified cartilage (cc), and subchondral bone quality, while the other one was examined by confocal microscopy to evaluate cell viability. The histological examination showed a normal matrix and cell distribution of the cartilage, while the cc showed lacunae ingrowing from the underlying bone. The subchondral bone showed normal lamellae and histology, and the healing of the flap. Confocal microscopy showed almost exclusively viable chondrocytes. This demonstration of non-injured cartilage at short-term follow-up together with promising clinical and radiological 2- and 5-year follow-up results indicate a potential promising outlook for the long term, as further chondral damage is not expected. So trochleoplasty can be seen as a primary intervention for patellar instability because of trochlear dysplasia as the risk for cartilage damage is low.