When Rupert and Pong Ping journey to China, the Emperor's pet dragon becomes jealous of Pong Ping and has him kidnapped by a ferocious fire-breathing relative. Rupert rescues Pong Ping, and seals the friendship between the Emperor and his pet dragon.

When a young magician Rupert's age threatens the last herd of unicorns, Rupert and his friend Tiger Lily fly to mythical Um Island. There they not only help a timid young unicorn learn to stand up to his problems, but teach the young magician a lesson about growing up.

Algy learns a lesson about letting his curiosity get the better of him when he accidentally sends himself back to medieval England in The Wise Old Goat's time machine. It's up to Rupert to follow Algy and rescue him from the hands of an evil knight.

When Rupert and Podgy find what appear to be purple cakes in the forest, Podgy ignores Rupert's warnings and eats them. Too late, he discovers that they are The Professor's creations, devised to make things lighter than air. In danger of floating helplessly into space, Podgy is saved by Rupert and learns never to eat anything unless you know exactly what it is and where it came from.

Rupert and his friend, Bill Badger, learn that there are some things more important than winning when they find themselves on opposing sides in the ultimate game that could well destroy Gameland.

Rupert chooses to work around his friend, Officer Growler, and the laws he represents in order to free a rare baby abominable snowman from the influential Sir Jasper. However, it's only when he plays by Growler's rules is he able to help his new friend and understand that, although it might seem slow, the law is fair and just and does punish the wrongdoers.

Rupert loses his battle to break an age-old tradition when his attempts to kindle a friendship between a knight and a fire-breathing dragon ultimately end up with them engaged in a duel to the death. Only afterward does Rupert realize that the fight was staged and now, having done what was traditionally expected of them, the dragon and knight can co-exist as friends.

When his appetite ultimately gets himself and Rupert caught by hungry crocodiles, Podgy promises to change. However, it's also his appetite that allows them to escape, allowing Rupert to learn to accept others for what they are, faults included.

Rupert's unsuccessful attempts to teach a cantankerous wood troll the meaning of friendship only causes problems for the Imps of Spring, hard pressed to bring spring to Nutwood on time. Only when Rupert allows their Wand of Spring to be destroyed in order to save the troll from his own mischief does the troll finally understand what being a friend is all about.

When Rupert is falsely accused, caught and tried by King Neptune's undersea court for kidnapping his prized Whistle Fish, it's up to Rupert and a little mermaid to race against time and save the Fish, demonstrating that creatures of the land and sea must work together for the benefit of all.

Tricked by an evil sorcerer into putting Tiger Lily under a sleeping spell, Rupert flies to the Bird Kingdom, hoping to find the cure. However, it's only when he learns to read between the lines that he's able to find the way to awaken his friend.

Rupert's old snowman has fled to Nutwood seeking refuge from Billy Blizzard. Rupert learns that Blizzard has frozen King Frost and all the snowmen. Rupert and his snowman, as well as Reika, one of Santa's elves, must now head to the North Pole and end Billy's reign of terror.

When Rupert finds a treasure map in the hull of a model ship, he convinces three retired pirates to get up out of their rocking chairs and go after it. In so doing, the ancient mariners recapture their bygone days and ultimately realize that life isn't over just because they are old.