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, Winnie the Pooh, Piglet, Tigger, Rabbit, Eeyore, The Vultures, and Jiminy Cricket entered Sherwood Forest and met Robin Hood and Little John (who is revealed to be Pooh's 2nd cousin) 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 Pooh 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 Pooh, Piglet, Tigger, Rabbit, and Eeyore joins him and competes against the Sheriff and others. The Vultures hid on top the Royal Box so Prince John doesn't see them and Jiminy hids in Little John's pockets. Hiss discovers Robin's and Pooh and his friends' 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, Pooh and the others, and Prince John's soldiers. Robin and Maid Marian are reunited, and the townsfolk (along with 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 Pooh and the others to rescue him. On the night before Friar Tuck's hanging, Robin, Pooh, Rabbit, and the Vultures steals a large amount of taxation money from Prince John's bedroom while Little John, Piglet, Tigger, Eeyore, and Jiminy frees Friar Tuck and the other townsfolk, who all escape on a cart. Pooh and the others also joins 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 Pooh 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. Pooh and the others rode off into the sunset to see what new adventure awaits them.
- This film features the first debut of Jiminy Cricket.
- Little John is revealed to be Pooh's 2nd cousin.
- Skippy the Bunny and his family are revealed to be Rabbit's relatives since they're rabbits..
- This is the first time that Toonguy500 has written a Winnie the Pooh crossover with a classic Disney film.
- This is the first film that DisneyDaniel93 and Toonguy500 worked together on.
- Most people wondered why Prince John should've told Owl and Gopher to be quiet during the "No Chance" song. This was because Little John was confronting Prince John while the two sang the song.
- This is a PAL film with PAL bits from The Many Adventures of Winnie the Pooh, Pooh's Grand Adventure: The Search For Christopher Robin, Piglet's Big Movie, Pooh's Heffalump Halloween Movie, The Jungle Book,Pinocchio, and Fun and Fancy Free and NTSC bits from The Tigger Movie, Pooh's Heffalump Movie, Winnie the Pooh: A Very Merry Pooh Year, Mickey's Christmas Carol, and The Jungle Book 2.
- During the part where Pooh and the others met Robin Hood and Little John, Buzzie the Vulture mentions Baloo's name when he said to Pooh, "Hey, Pooh, I thought Baloo was your Cousin."
- Winnie the Pooh, Piglet, Tigger, Rabbit, and Eeyore will face Prince John again in Winnie the Pooh in Fantasmic! (Tokyo Disney Sea).