Abstract Recent evidence suggests a stabilizing effect of crop diversity on agricultural production. However, different methods are used for assessing these effects and there is little systematic quantitative evidence on diversification benefits. The aim of this study was to assess the relationship between volatility of combined crop yields (denoted as standard deviation) and diversity (denoted as Shannon’s Evenness Index SEI) for standardized yield data of major crop species grown in Germany between 1977 and 2018 (winter wheat, winter barley, silage maize and winter rapeseed) at the county level. Portfolio theory was used to estimate the optimal crop area share for minimizing yield volatility. On average, results indicated a weak negative relationship between volatility and the SEI during the past decades for the case of Germany. Optimizing crop area shares for minimizing volatility reduced yield variance on average by 24 % but was associated with a decrease in SEI for most counties. This was related to the finding that the stability of individual species, i.e., barley and wheat, was more effective in reducing the volatility of combined yields than the asynchronous variation in annual yields among crops. Future studies might include an increased number of crop species and consider temporal diversification effects for a more realistic assessment of the relation between yield volatility and crop diversity and test the relationship in other regions and production conditions.