Abstract: This study shows an average yield increase of 415–1,338 kg ha−1 per unit increase of the Shannon diversity index for feed barley cultivar use. There is a global quest to increase food production sustainably. Therefore, judicious farmer choices such as selection of crop cultivars are increasingly important. Cultivar diversity is limited and, as a consequence, corresponding crop yields are highly impacted by local weather variations and global climate change. Actually, there is little knowledge on the relationships between yields of regional crops and cultivar diversity, that is evenness and richness in cultivar use. Here, we hypothesized that higher cultivar diversity is related to higher regional yield. We also assumed that the diversity-yield relationship depends on weather during the growing season. Our data were based on farm yield surveys of feed and malting barley, Hordeum vulgare L.; spring wheat, Triticum aestivum L.; and spring turnip rape, Brassica rapa L. ssp. oleifera, from 1998 to 2009, representing about 4,500–5,500 farms annually. We modeled the relationships between regional yields and Shannon diversity indices in high-yielding (south-west) and low-yielding (central-east) regions of Finland using linear mixed models. Our results show that an increase of Shannon diversity index increases yield of feed barley. Feed barley had also the greatest cultivar diversity. In contrast, an average yield decrease of 1,052 kg ha−1 per unit increase in Shannon index was found for spring rape in 2006 and 2008. Our findings show that cultivar diversification has potential to raise mean regional yield of feed barley. Increasing cultivar diversity thus offers a novel, sustainability-favoring means to promote higher yields.