While many studies comparing atmospheric reanalysis and surface observations have focused on the similarity of mean fields, trends, or frequencies of extreme events, very few have assessed how similar surface observations and reanalysis data sets are in terms of their specific identification of extreme temperature event days. Here, we assess the similarity between surface observations and three reanalysis products: ERA5, ERA5-LAND, and NARR, in terms of the days on which they identify extreme temperature events. We assess similarity from 1979-2016 for 231 locations in the United States and Canada, assessing Extreme Heat and Cold Event days, as well as their counterpart events that are relative for the time of year. Cold Events have a greater match than Heat Events. ERA5 has the greatest match percentage with station data across the study region. Match percentage is greatest in mid-latitude, continental locations, with poorer performance in coastal areas, and the Arctic.