We study the asymptotic dynamics of a driven quantum two level system coupled via a quantum detector to the environment. We find multi-photon resonances which are due to the entanglement of the qubit and the detector. Different regimes are studied by employing a perturbative FloquetBorn-Markov approach for the qubit+detector system, as well as non-perturbative 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.PACS numbers: 03.65. Yz, 42.50.Hz, 03.67.Lx, 74.50.+r A prominent physical model to study dissipative and decoherence effects in quantum mechanics is the spinboson model [1]. Currently, we witness its revival since it allows a quantitative description of solid-state quantum bits (qubits) [2]. A more realistic description requires the inclusion of the external control fields as well as the detector. In the spin-boson model, the environment is characterized by a spectral density J(ω). In its widest used form, J(ω) is proportional to the frequency ω mimicking the effects of an Ohmic electromagnetic environment. However, if the environment is formed by a quantum detector which itself is damped by Ohmic fluctuations, the simple Ohmic description might become inappropriate. As an example, we focus on a superconducting ring with three Josephson junctions (so termed flux-qubit). It is read out by a dc-SQUID [3, 4, 5] whose plasma resonance at Ω p gives rise to an effective spectral density J eff (ω) for the qubit with a peak at Ω p [6], cf. Eq. (4) below. Recently, the coherent coupling of a single photon mode and a superconducting charge qubit has also been studied [7]. Until now, the effects of such a structured spectral density on decoherence and in presence of a resonant control field have only been studied in [8,9] within a perturbative approach in J eff . It was shown in [10,11] for the static case that a perturbative approach breaks down for strong qubit-detector coupling, and when the qubit and detector frequencies are comparable.In the presence of microwaves, multi-photon resonances are expected to occur when the frequency of the ac-field, or integer multiples of it, match characteristic energy scales of the system [12]. Such multiphoton resonances can be experimentally detected in an ac-driven flux qubit by measuring the asymptotic occupation probabilities of the qubit, as the dc-field is varied [3,13]. These "conventional" resonances, which have also been theoretically investigated in [14], could be explained in terms of intrinsic transitions in a driven spin-boson system with an unstructured environment.In this Letter, we investigate the asymptotic dynamics of a quantum two state system (TSS) with a structured FIG. 1: Schematic picture of the models we use. In (a) the system is a two-level-system (TSS) coupled to a harmonic oscillator with the latter coupled to an Ohmic environment with spectral density J Ohm (ω). In (b), the TSS is couple...