Technical Abstract: Consumer demand regarding the impacts of conventional agriculture on the environment and human health have spurred the growth of organic farming systems; however, organic agriculture is often criticized as low-yielding and unable to produce enough food to supply the world’s population. Using wheat as a model crop species, we show that poorly adapted cultivars are partially responsible for the lower yields often found in organic farming systems when compared with conventional farming systems. Our results demonstrate that the highest yielding soft white winter wheat genotypes in conventional systems are not the highest yielding genotypes in organic systems. An analysis of variance for yield among 35 genotypes between paired organic and conventional systems showed highly significant (P < 0.001) genotype x system interactions in four of five locations. Genotypic ranking analysis using Spearman’s rank correlation coefficient (RS) showed no correlation between genotypic rankings for yield in four of five locations; however, the ranks were correlated for test weight at all five locations. This indicates that increasing yield in organic systems through breeding will require direct selection within organic systems rather than indirect selection in conventional systems. Direct selection in organic systems produced yields 15%, 7%, 31% and 5% higher than the yields resulting from indirect selection for locations one through four, respectively. With crop cultivars bred in and adapted to the unique conditions inherent in organic systems, organic agriculture will be better able to realize its full potential as a high-yielding alternative to conventional agriculture.