Observed changes in Northern Hemisphere snow cover from satellite records were compared to those predicted by all available Coupled Model Intercomparison Project Phase 5 (“CMIP5”) climate models over the duration of the satellite’s records, i.e., 1967–2018. A total of 196 climate model runs were analyzed (taken from 24 climate models). Separate analyses were conducted for the annual averages and for each of the seasons (winter, spring, summer, and autumn/fall). A longer record (1922–2018) for the spring season which combines ground-based measurements with satellite measurements was also compared to the model outputs. The climate models were found to poorly explain the observed trends. While the models suggest snow cover should have steadily decreased for all four seasons, only spring and summer exhibited a long-term decrease, and the pattern of the observed decreases for these seasons was quite different from the modelled predictions. Moreover, the observed trends for autumn and winter suggest a long-term increase, although these trends were not statistically significant. Possible explanations for the poor performance of the climate models are discussed.