We investigate the non-equilibrium quantum dynamics of a canonical light-matter system, namely the Dicke model, when the light-matter interaction is ramped up and down through a cycle across the quantum phase transition. Our calculations reveal a rich set of dynamical behaviors determined by the cycle times, ranging from the slow, near adiabatic regime through to the fast, sudden quench regime. As the cycle time decreases, we uncover a crossover from an oscillatory exchange of quantum information between light and matter that approaches a reversible adiabatic process, to a dispersive regime that generates large values of light-matter entanglement. The phenomena uncovered in this work have implications in quantum control, quantum interferometry, as well as in quantum information theory.