Ultra-high-performance concrete (UHPC) has been widely utilised in strengthening and rehabilitating conventional normal concrete (NC) structures due to its exceptional mechanical properties and durability. However, in cold climates, the interfacial bond between UHPC and NC is susceptible to degradation under freeze–thaw cycles, potentially compromising the composite action and long-term performance of strengthened structures. This study systematically investigated the shear behaviour of a UHPC-NC interface with planted reinforcement subjected to various freeze–thaw conditions. The experiments were conducted considering different numbers of freeze–thaw cycles (0, 20, 40, 60, 80, and 100) and salt solution concentrations (0%, 3.5%, and 5%). Direct shear tests were performed to evaluate interfacial failure modes, mass loss, and shear strength degradation. Results identified three characteristic failure modes: adhesive debonding at the interface, mixed failure involving both the interface and the NC substrate, and crushing failure within the NC substrate. Specimens exposed to 3.5% salt solution experienced the most significant deterioration, exhibiting a 35% reduction in shear strength after 100 freeze–thaw cycles. Normally, lower salt concentrations were found to induce greater interfacial damage compared to higher concentrations. The study underscores the importance of increasing the embedment depth of the planted reinforcement to alleviate stress concentration and enhance interfacial durability in freeze–thaw environments.