Cross-species annotation transfer is a widely used approach for transferring information about simple molecular functions or pathways from one protein in one species to its ortholog in another species. In crop species, the phenotypic traits of interest, such as grain yield, are very complex and are often related to multiple biological processes and systems. It is still unclear to what extent the high level annotations describing phenotypic traits can also be reliably transferred across species. In this work, we have developed a procedure to measure precisely the transferability of these functional annotations from one species to another and demonstrate its application to Arabidopsis and several crop species. This comparative analysis is a step towards assigning higher level biological function to genes and gene networks as part of the wider genotype to phenotype challenge.