Cold drawing is a commonly used technique for manufacturing the prestressing steel wires used as structural elements in prestressed concrete structures. As a result of this manufacturing process, a non-uniform plastic strain and residual stress states are generated in the wire. These stress and strain fields play a relevant role as the main cause of the in-service failure of prestressing steel wires in the presence of an aggressive environment, hydrogen embrittlement (HE). In this paper, hydrogen susceptibility to HE is compared in two different commercial cold-drawn wires with the same dimensions at the beginning and at the end of manufacturing that follow different straining paths. To achieve this goal, numerical simulation with the finite element (FE) method is carried out for two different industrial cold-drawing chains. Later, the HE susceptibility of both prestressing steel wires was estimated in terms of the hydrogen accumulation given by FE numerical simulations of hydrogen diffusion assisted by stress and strain states, considering the previously obtained residual stress and plastic strain fields generated after each wire-drawing process. According to the obtained results, the hardening history modifies the residual stress and strain states in the wires, affecting their behavior in hydrogen environments.