Life at the Rainy Color café can never be described as boring. The arrival of the Koga brothers from England—Noel, always brimming with curiosity, and Nicola, somewhat shy and conservative—ensures that their sibling, café manager Shion, is kept on his toes. There's also another newcomer, cameraman/photographer Jun Arisawa, who holds a mysterious connection to café owner Koji Amami. Last but not least, there's a special photograph that incites all kinds of heartfelt and comedic reactions from the Rainy Color crew!

Headmasters starts with Galvatron leading a new batch of Destrons to wage war on Cybertron, the Destron Headmasters. The Cybertrons are rescued by the arrival of the Cybertron Headmasters, led by Fortress (Cerebros, the head of Fortress Maximus). It is revealed that Fortress Maximus left Cybertron millions of years ago in search of energy, and have finally managed to come home. He explains that the Headmasters are from a planet called Master; the human-sized robots who live there built themselves Transformers-sized bodies. They can then transform themselves into the heads of the robots, and have now joined the Cybertron-Destron war.

Following the destruction of the magical floating device from OVA 1, the Magic Academy falls to earth, but unfortunately lands on and breaks a demon seal, releasing hundreds of ancient demons into the forest around the academy. The teachers are barely keeping the demons away and are desperately searching for the pieces of the floating device, so to earn more magic stones, all of the students from Amelia's class decide to leave the academy (even though they were told not to) to find the missing pieces.

There is a magical academy that is located on a floating island in the sky. This OVA is about the students of one of the academy's classes, who's only chance not to fail the semester is to win a competition where they must show off their magic skills.