The phenomenon of dynamic matching was proposed by Carpenter nearly four decades ago. In this work, we perform detailed dynamical studies of the original model studied by Carpenter. Existence of competing mechanisms that influence the extent of dynamic matching with varying depth of the caldera well, as noted by Carpenter, is confirmed. A phase space dynamical viewpoint is provided for the origin of the competing mechanisms. Our results show that the extent of dynamic matching is significantly influenced by the amount of excess energy above the transition state that controls the entrance into the caldera region. Moreover, we find that dynamic matching can persist for fairly deep caldera wells. Quantum dynamical studies are performed to assess the extent of classical-quantum correspondence in the system and the robustness of the dynamic matching mechanism.