In the short, a hunt for a lost sheep turns into a competition between Hiccup and his friends for the first title of Dragon Racing Champion of Berk.

Afterwards, Tuffnut has just finished his new creepy-looking face paint which shocks Astrid, Hiccup and Toothless.

Snotlout arrives cheering that his new Sheep Launcher finally worked, which Astrid points out that it took him thirty-two tries to get it right.

It cuts to a flashback, shortly after the events of the second season where the Riders are still in their early teens.

Berk is getting ready for the traditional annual boat race called the Regatta which starts in a few days, when suddenly a herd of sheep run throughout the village, causing minor trouble.

Sven then cries out, alarmed that his prized black sheep is still missing and hoping that it didn't fall down the well again.

Fishlegs then helps Meatlug board a ship covered in a big cloth, which is hiding what he is working on.

Fishlegs considers himself to be a sailor at heart and is excited that he is now finally old enough to compete; he and Meatlug will be working on their ship until the Regatta.

Meanwhile, at the Academy, Tuffnut is plotting out some rules for the Riders' sheep competition, but is interrupted as Hiccup arrives reluctantly prohibiting them to carry on with their plan as he has Stoick's strict orders to prepare for the Regatta.

Later, the villagers gather at the Great Hall, growing restless for entertainment and they want to see the Dragon Race again.

Astrid then says to Hiccup that Stoick isn't going to be back for a few days and points out that the Dragon Race is also a great way to blow off steam.

Hiccup and Astrid then go to get Fishlegs, but after mocking the name 'Snotnuts' he declines joining the race as he and First Mate Meatlug are still too busy getting ready for the Regatta, refusing to back down on his family tradition.

After he unveils the small ship with a flourish, Toothless can't help but laugh at the decorations.

Just as the flag is about to be dropped, Stoick is suddenly heard screaming Hiccup's name: he has returned earlier than expected.

Stoick then proclaims that the team who wins the race will have their portrait hung in the Great Hall, and a feast thrown in their honor.

Hiccup quickly sets Toothless' tail to boost their speed and is able to snatch the sheep before Snotlout does.

Meanwhile, the twins attempt to cheat by stealing sheep that are not Silent Sven's to quickly double their points, but Astrid arrives before they can grab any.

When it is proclaimed by Astrid that the teams are all tied up, Stoick announces that whoever finds the black sheep wins.

The flashback ends and it goes back to the present time, with Hiccup concluding that it technically was Tuffnut who invented Dragon Racing (because he was the one came up with the concepts of the rules) humiliating the three of them, especially Snotlout, who is deeply depressed.

When Hiccup just tells them that they should say that they all invented Dragon Racing the Twins reluctantly accept, but Tuffnut still claims that Snotlout did nothing.

Then a horn is heard, signalling that it is time for the Dragon Race and all the Riders quickly set off to start.