How to Train Your Dragon - Release order
Dragons: Dawn of the Dragon Racers

7.- Dragons: Dawn of the Dragon Racers (2014)
Dawn of the Dragon Racers, is a short film describing how Dragon Racing was invented. Hiccup and all his friends from the dragon academy fight about who really invented it.
How to Train Your Dragon: The Hidden World

9.- How to Train Your Dragon: The Hidden World (2019)
As Hiccup fulfills his dream of creating a peaceful dragon utopia, Toothless' discovery of an untamed, elusive mate draws the Night Fury away. When danger mounts at home and Hiccup's reign as village chief is tested, both dragon and rider must make impossible decisions to save their kind.
How to Train Your Dragon: Homecoming

10.- How to Train Your Dragon: Homecoming (2019)
Hiccup and Toothless reunite to remind both their kinds of the inseparable bond between vikings and dragons.