His first major role was in "Lord of the Rink". Derek first appears when the Ice Hockey team is practicing Ice Hockey on the team and the Enchanted Ice Dancing Class are practicing Enchanted Ice Dancing. While Hugo is distracted by the Enchanted Ice Dancing, Derek takes the puck from him but Hugo takes it back and scores. After Sofia accidentally sends herself sliding across the rink, Derek and the other princes, except Hugo, leave the rink, after Sir Henley decided the rink sharing idea was not working out. Hugo later tells him he won't be coming to Ice Hockey Practice because he's sick.
Some time later, Hugo arrives at Hockey practice seemingly feeling better. At the time, Derek notices Hugo's odd behavior and wonders what he is up too. Derek soon finds out and catches Hugo doing Enchanted Ice Dancing. Derek proves to be a bit disloyal about it. When Hugo tells the hockey team "Go ahead; make fun of me", Derek almost takes it seriously only to be stopped by James. At Sofia and James's urging, Derek tells Hugo he is okay with it. Later, like the rest of the hockey team, Derek is surprised that Hugo is not at his ice-dancing recital. When Sofia arrives and takes Hugo to the recital, Derek and the rest of the hockey team take off after them to see Hugo ice-dance. At the recital, Derek is so impressed by Hugo's amazing talent that he asks him to teach him how to do all those flips. When Flora put a magic spell on his hockey skates, Derek finds himself having more trouble at ice-dancing than Sofia did. The spell on his skates sends him spinning in the air, calling "How do I stop spinning?!", prompting Sofia and Hugo to go after him.