Due to the combined influence of traffic loading and environment, the structural condition of pavement deteriorates with time. Studies on structural damage, which usually results in functional deterioration, is important for the highway engineer to plan the maintenance/strengthening strategies to extend the life of pavements. In the present investigation, the data collected under the R-6 research project of the Ministry of Surface Transport, India, has been used to develop prediction models and growth curves for rebound deflection, rut depth, and crack area of pavements considering two types of surfacing: BM (bituminous macadam) + PC (premix carpet) and BM + AC (asphaltic concrete), commonly practiced in India. The performance of the pavements were studied and comparative analysis was made in terms of growth in deflection, rut depth, and crack area. An attempt has been made to develop failure envelopes based on selected critical rut depth criteria. The results are useful to decide the timing for maintenance/rehabilitation programs.