The impact of adverse weather conditions (AWCs) on crop production is random in both time and space and depends on factors such as severity, previous agrometeorological conditions, and plant vulnerability at a specific crop development stage. Any exclusion or improper treatment of any of these factors can cause crop models to produce significant under- or overestimates of yield. The analysis presented in this paper focuses on a range of agrometeorological indices (AMI) related to AWCs that might affect real yield as well as simulated yield. For this purpose, the analysis addressed four indicators of extreme temperatures and three indicators of dry conditions during the growth period of maize and winter wheat in Austria, Croatia, Serbia, Slovakia, and Sweden. It is shown that increases in the number and intensity of AWCs cannot be unambiguously associated with increased deviations in simulated yields. The identified correlations indicate an increase in modeling uncertainty. This finding represents important information for the crop modeling community. Additionally, it opens a window of opportunity for a statistical (“event scenario”) approach based on correlations between agrometeorological indices of AWCs and crop yield data series. This approach can provide scenarios for certain locations, crop types, and AWC patterns and, therefore, improve yield forecasting in the presence of AWCs.