To elucidate the degradation mechanism of expansive soil–rubber fiber (ESR) under freeze–thaw cycles, freeze–thaw cycle tests and consolidated undrained tests were conducted on the saturated ESR. The study quantified the elastic modulus and damage variables of ESR under different numbers of freeze–thaw cycles and confining pressure, and proposed a damage constitutive model for ESR. The primary findings indicate that: (1) The effective stress paths of ESR exhibit similarity across different numbers of freeze–thaw cycles, the critical stress ratio slightly decreased by 8.8%, while the normalized elastic modulus experienced a significant reduction, dropping to 42.1%. (2) When considering the damage threshold, the shear process of ESR can be divided into three stages: weak damage, damage development, and failure. As strain increases, the microdefects of ESR gradually develop, penetrating macroscopic cracks and converging to form the main rupture surface. Eventually, the damage value reaches 1. (3) Due to the effect of freeze–thaw cycles, initial damage exists for ESR, which is positively correlated with the number of freeze–thaw cycles. The rubber fibers act as tensile elements, and the ESR damage evolution curves intersect one after another, showing obvious plastic characteristics in the late stage of shear. (4) Confining pressure plays a role in limiting the development of ESR microcracks. The damage deterioration of ESR decreases with an increase in confining pressure, leading to an increase in ESR strength. (5) Through a comparison of the test curve and the theoretical curve, this study validates the rationality of the damage constitutive model of ESR under established freeze–thaw cycles. Furthermore, it accurately describes the nonlinear impact of freeze–thaw cycles and confining pressure on the ESR total damage.