The Flying Crown trophy is the greatest prize in royal sport, and according to Princess Clio, the Junior Knights win the trophy every year. Nobody in Prince Hugo's family has ever won the championship race or the Flying Crown until he himself and Sofia won. According to Amber, Royal Prep hasn't made it to the championships in a century.
In the beginning of the episode "The Flying Crown", Sofia and her big brother, James, won the latest flying derby race and were moving onto the championships, where they were going to race for the Flying Crown trophy against the Junior Knights Academy. James was really excited about riding in this race and doing his and Sofia's best team plays until he fell down and sprained his wrist. Since James couldn't ride in the championship race with his younger sister, Sofia found herself paired up with her old flying derby rival, Prince Hugo, who really wasn't interested in practicing team plays and was determined to cross the finish line first.
Later in the episode, when Hugo's flying horse, Electra, told Sofia that Hugo hadn't had a chance to hear the Royal Prep cheer, she learned that Hugo was feeling left out, and she managed to reason with him about this. Hugo told her that his older brother, Axel, their father, uncle, and grandfather were on the flying derby team when they were each at Royal Prep, and Sofia knew that none of them won the championship race and the Flying Crown. She told Hugo that they had a chance to do that as long as they did the flying slingshot in order to beat Squires Vaughan and Vance. She also told him that not only would they win the trophy, but Hugo would become the first in his family to do that, and the school would cheer for him.
During the championship race, Sofia and Hugo successfully did the flying slingshot and won the trophy much to the surprise of their opponents. Not only did Hugo have a chance to hear the Royal Prep cheer and become the first in his family to win the Flying Crown, but this is also how he became friends with Sofia because she taught him the true meaning of teamwork and the importance of working together.
Since the Junior Knights won the trophy every year, they lost the trophy and the championship race for the very first time in The Flying Crown.
Prince Hugo is the first member of his family to ever win this trophy.