We study the asymptotic dynamics of a driven quantum two-level system coupled via a quantum detector to the environment. We find multiphoton resonances which are due to the entanglement of the qubit and the detector. Different regimes are studied by employing a perturbative Floquet-Born-Markov approach for the qubit+detector system, as well as nonperturbative real-time path integral schemes for the driven spin-boson system. We find analytical results for the resonances, including the red and the blue sidebands. They agree well with those of exact ab initio calculations.