Frequency shifts of red- and blue-scattered (Stokes/anti-Stokes) side-bands in quantum optomechanics are shown to be counter-intuitively inequal, resulting in an unexpected symmetry breaking. This difference is referred to as Side-band Inequivalenve (SI), which normally leans towards red, and being a nonlinear effect it depends on optical power or intracavity photon number. Also there exists a maximum attainable SI at an optimal operation point. The mathematical method employed here is a combination of operator algebra equipped with harmonic balance, which allows a clear understanding of the associated nonlinear process. This reveals the existence of three distinct operation regimes in terms of pump power, two of which have immeasurably small SI. Compelling evidence from various experiments sharing similar interaction Hamiltonians, including quantum optomechanics, ion/Paul traps, electrooptic modulation, Brillouin scattering, and Raman scattering unambiguously confirm existence of a previously unnoticed SI.