The advent of the silicon photomultiplier has allowed the development of highly segmented calorimeters using plastic scintillator as the active media, with photodetectors embedded in the calorimeter, in dimples in the plastic. To reduce the photodetector’s dark current and radiation damage, the high granularity calorimeter designed for the high luminosity upgrade of the CMS detector at CERN’s Large Hadron Collider will be operated at a temperature of about −30 °C. Due to flammability considerations, a low oxygen environment is being considered. However, the radiation damage to the plastic scintillator during irradiation in this operating environment needs to be considered. In this paper, we present measurements of the relative decrease of light output during irradiation of small plastic scintillator tiles read out by silicon photomultipliers. The irradiations were performed using a 60Co source both to produce the tiles’ light and as a source of ionizing irradiation at dose rates of 0.3, 1.3, and 1.6 Gy/h, temperatures of −30, −15, −5, and 0 °C, and with several different oxygen concentrations in the surrounding atmosphere. The effect of the material used to wrap the tile was also studied. Substantial temporary damage, which annealed when the sample was warmed, was seen during the low-temperature irradiations, regardless of the oxygen concentration and wrapping material. The relative light loss was largest with 3MTM Enhanced Specular Reflector Film wrapping and smallest with no wrapping, although due to the substantially higher light yield with wrapping, the final light output is largest with wrapping. The light loss was less at warmer temperatures. Damage with 3% oxygen was similar to that in standard atmosphere. Evidence of a plateau in the radical density was seen for the 0 °C data.