Data competitions have become a popular approach to crowdsource new data analysis methods for general and specialized data science problems. In plant phenotyping, data competitions have a rich history, and new outdoor field datasets have potential for new data competitions. We developed the Global Wheat Challenge as a generalization competition to see if solutions for wheat head detection from field images would work in different regions around the world. In this paper, we analyze the winning challenge solutions in terms of their robustness and the relative importance of model and data augmentation design decisions. We found that the design of the competition influence the selection of winning solutions and provide recommendations for future competitions in an attempt to garner more robust winning solutions.