The entropy inequality, commonly taken as an axiom of continuum mechanics, is found to be spontaneously violated in macroscopic granular media undergoing collisional dynamics. The result falls within the fluctuation theorem of nonequilibrium thermodynamics, which is known to replace the Second Law for finite systems. This phenomenon amounts to the system stochastically displaying negative increments of entropy. The focus is on granular media in Couette flows, consisting of monosized circular disks (with 10 to 104 disks of diameters 0.01 m to 1 m) with frictional-Hookean contacts simulated by molecular dynamics accounting for micropolar effects. Overall, it is determined that the probability of negative entropy increments diminishes with the Eulerian velocity gradient increasing, while it tends to increase in a sigmoidal fashion with the Young modulus of disks increasing. This behavior is examined for a very wide range of known materials: from the softest polymers to the stiffest (i.e., carbyne). The disks’ Poisson ratio is found to have a weak effect on the probability of occurrence of negative entropy increments.