Roary and Theodore's Adventures of Robin Hood is a Roary the Racing Car/Theodore Tugboat/Disney crossover film.
The film is narrated by a rooster minstrel named Alan-a-Dale (mentioned verbally only, while credited officially on-screen as "The Rooster") who describes Robin Hood and Little John as outlaws who dwell in Sherwood Forest, stealing from the rich and giving to the poor people of Nottingham. They are constantly pursued by the Sheriff of Nottingham and his men. One day, (along with ) entered Sherwood Forest and met Robin Hood and Little John and they join the two in their adventures. Prince John, the ruling king of England passes through Nottingham. After his servant Sir Hiss hypnotised King Richard into going to battle in The Crusades, Prince John made himself king and began collecting taxes from the people of England to become richer. Robin and Little John disguise themselves as a female fortune tellers and manage to steal from Prince John with Roary, Theodore, Thomas, Twilight and the others helping.
Robin is romantically infatuated with Maid Marian who shares his feelings, although they have not seen each other for years. An opportunity arises for their reunion when Prince John announces an archery tournament, the winner receiving a kiss from Maid Marian and a golden arrow from Prince John. Robin enters the tournament disguised as a chatty stork from Devonshire and join him and compete against the Sheriff and others. The hid on top the Royal Box so Prince John doesn't see them and hid in Little John's pockets. Hiss discovers Robin's and identity but is trapped in a barrel of ale by Friar Tuck and Alan-a-Dale. Robin wins, but his disguise is blown by Prince John who orders him, Pooh, and his friends to be executed. Little John, who has been disguised as the Duke of Chutney, threatens Prince John, starting a battle between Robin, Little John, Roary, Theodore, Thomas, Twilight and the others, and Prince John's soldiers. Robin and Maid Marian are reunited, and the townsfolk (along with all our heroes) all retreat into Sherwood Forest where they dub Prince John as the "Phony King of England".
Enraged by this, Prince John maximises taxes to impossible amounts and all who cannot pay are put in prison. Alan-a-Dale is among the unfortunate ones. The Sheriff visits Friar Tuck's church where he steals money from a poor box, enraging Friar Tuck into attacking the Sheriff, leading to his arrest. Prince John decides to hang Friar Tuck, prompting Robin, Little John, and Roary, Theodore, Thomas, Twilight and the others to rescue him. On the night before Friar Tuck's hanging, Robin, steal a large amount of taxation money from Prince John's bedroom while Little John, free Friar Tuck and the other townsfolk, who all escape on a cart. Roary, Theodore, Thomas, Twilight and all their friends also join with the townsfolk. The Sheriff confronts Robin in Prince John's castle and sets the castle on fire. Robin is forced to flee to the spire of the castle but falls into a river, seemingly shot by archers. He survives, much to Prince John's anger, and the destruction of the castle which belonged to John's beloved mother, sends him over the edge.
Later, King Richard returns and pardons Robin, Little John, and Roary, Theodore, Thomas, Twilight and the others, and forces Prince John, Hiss and the Sheriff to do hard labour. Robin and Maid Marian get married and depart to places unknown with Little John and a young rabbit named Skippy in tow. Roary, Theodore and the others rode off into the sunset to see what new adventure awaits them while Thomas, Twilight and their team returned to Equestrisodor.
- are guest starring in this film.