Pomegranate cv. ‘Wonderful’ fruit are susceptible to chilling injuries of the peel (CIp) when stored at 7 °C in modified-atmosphere bags for more than 3 months. The damage, manifested as superficial browning, is restricted to the fruit skin, i.e., the outer colored layer of the peel. To characterize possible causes of CIp development, fruit were collected at early harvest—when the premature fruit are poorly colored and susceptible to CIp development, and at late harvest—when mature fruit have fully red skin and less susceptibility to CIp. Skin samples were collected on day of harvest and at different time points during storage. Anatomical study of skin with CIp disorder showed a broken cuticle layer with underlying degenerated cells. A high total phenol content, which is associated with high antioxidant capacity, was not sufficient to prevent the development of CIp in the premature fruit. The concentration of punicalagin was the same for premature and mature skin at harvest and during storage, and therefore not associated with CIp development in the premature fruit skin. Furthermore, the expression of antioxidant-related genes CAT2, SOD and GR2 was similar for both premature and mature fruit skin. Poor pigmentation of the premature fruit skin and chilling-induced downregulation of key anthocyanin-biosynthesis genes were associated with CIp development. High total phenol concentration combined with high expression of the gene encoding PPO was also associated with CIp; however, high expression ratio of PAL to PPO was found in mature skin, and may be associated with reduced CIp disorder. The results presented suggest future possibilities for controlling the CIp phenomenon.