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We report the experimental observation of high-order sideband transitions at the single-photon level in a quantum circuit system of a flux qubit ultrastrongly coupled to a coplanar waveguide resonator. With the coupling strength reaching 10% of the resonator's fundamental frequency, we obtain clear signatures of higher order red-sideband and first-order blue-sideband transitions, which are mainly due to the ultrastrong Rabi coupling. Our observation advances the understanding of ultrastrongly coupled systems and paves the way to study high-order processes in the quantum Rabi model at the single-photon level.