Jafar, Grand Vizier to the Sultan of Agrabah, is attempting to access the Cave of Wonders for a magical oil lamp containing a genie. He and his talking parrot, Iago, learn that only the metaphorical "Diamond in the Rough" can enter the cave.
Back in the Hundred Acre Woods, the first day of Autumn has arrived; to Winnie the Pooh it's another fun-filled season to be with his very best friend, Christopher Robin. However, he is nowhere to be found, which causes Pooh to worry what happened to him. After finding a sticky note revealing that Christopher Robin has been kidnapped, Owl scares Pooh and his friends when he reveals that Christopher Robin has been taken to Agrabah by Jafar. Pooh and his friends decided to head to Agrabah to save their friend. They arrive at Agrabah and meet Aladdin and his monkey, Abu and decide to wait on their journey to hang out with Aladdin and Abu.
In the meantime, Jasmine, the Sultan's daughter, frustrated with "having her life lived for her" and the obligation of marriage, goes to Agrabah's marketplace. She meets Pooh and his friends and street urchin Aladdin and his monkey, Abu who show her around the marketplace. Jafar, using a machine, discovers that Aladdin is the "diamond in the rough", and has him and Pooh and his friends captured. Jasmine orders him released, but Jafar lies, telling her Aladdin and our heroes are dead.
Jafar, disguised as an elderly man, releases Aladdin and Pooh and his friends from prison and leads them to the Cave of Wonders. The tiger-shaped head of the cave instructs them to touch nothing but the lamp. Aladdin and our heroes enter the cave and encounters a magic carpet before finding the lamp. Abu tries to steal a ruby which causes a cave-in, but the carpet helps them to the entrance. Jafar tries to kill Aladdin after getting the lamp, but Abu bites Jafar and takes the lamp back. Abu, the carpet and Aladdin and our heroes fall back into the cave just as it collapses.
When Aladdin awakens, he rubs the lamp, unleashing Genie who reveals he will grant Aladdin three wishes. Aladdin dupes Genie into freeing them from the cave without using up a wish. While contemplating his wishes, Aladdin asks Genie's opinion. Genie admits he would wish for freedom, since he has been a prisoner to his lamp for so long. Aladdin promises to later wish him free. For his first wish, Aladdin becomes a prince so he can marry Jasmine.
Back at the palace, Jafar makes plans to trick the Sultan into marrying Jafar to Jasmine, then kill both of them. His plans are interrupted when Aladdin parades into the Sultan's palace as "Prince Ali." Jasmine rejects him, considering him a buffoon. That night, Aladdin meets Jasmine, and takes her on a magic carpet ride. Jasmine realizes that Ali is the boy from the marketplace; Aladdin fabricates a story that he sometimes dresses as a "commoner" to escape palace life. Aladdin returns her home and they kiss.
After delivering Jasmine, Aladdin and Pooh and his friends are captured by Jafar who orders the guards to chain Aladdin and our heroes and throw them into the ocean. Aladdin summons Genie, who rescues Aladdin as his second wish. Aladdin and our heroes return to the palace, revealing the vizier's plot to Jasmine and the Sultan. Jafar realizes Aladdin's identity, also regonizes Pooh and his friends, and escapes from the Sultan's bodyguards. Surprised by Aladdin's bravery, the Sultan decides Aladdin should be his successor. Aladdin faces a moral dilemma, and decides to wait before wishing Genie free. Iago steals Genie's lamp and brings it to Jafar, who uses his first wish to become sultan. Jafar's second wish turns him into a powerful sorcerer sending Aladdin to a far-off place. With Aladdin taken care of and the world bowing to his knees, Jafar prepares for phase two of his master plan.
Aladdin uses the magic carpet to return to Agrabah. Jasmine distracts Jafar as Aladdin attempts to steal the lamp, but the vizier notices. In the midst of the battle, Jafar transforms into a giant cobra, much to the horror of Pooh and friends. Jafar boasts that he is "the most powerful being on Earth," only for Aladdin to remind him Genie is more powerful. Jafar uses his final wish to become a genie but forgets that genies are not free entities. Jafar is sucked into his new black lamp, draggin Iago with him. Genie flicks the lamp into the Cave of Wonders.
Aladdin finally wishes for Genie's freedom, much to Genie's surprise and happiness. Since Jasmine loves Aladdin, the Sultan changes the law so they can marry. Pooh and his friends went back to the Hundred Acre Wood. Genie leaves to explore the world while Aladdin and Jasmine celebrate their engagement..
- This film was requested by BowserMovies1989.
- The original version was an NTSC film with PAL bits from Pooh's Grand Adventure: The Search for Christopher Robin, Piglet's Big Movie, and Pooh's Heffalump Halloween Movie. The remake version is an NTSC film with NTSC bits from Winnie the Pooh and a Day For Eeyore, The Tigger Movie, The Book of Pooh: Stories From the Heart, Winnie the Pooh: A Very Merry Pooh Year, Pooh's Heffalump Movie, and Winnie the Pooh and PAL bits from The Many Adventures of Winnie the Pooh, Pooh's Grand Adventure: The Search for Christopher Robin, Piglet's Big Movie, Winnie the Pooh: Springtime with Roo, and Pooh's Heffalump Halloween Movie.
- Most of Daniel's original version does not have Pooh and Aladdin meet at all, this has angered many Pooh's Adventures fans and was declared as the worst Pooh's Adventures movie ever because of it.
- Prior to Daniel's remake version, the remake version where Pooh and Aladdin actually meet originally appeared on Yahoo! Video around 2010 and it was created by a different user, but was later removed.
- Pooh and his friends soon reunited with Genie in Pooh's Adventures of DuckTales the Movie: Treasure of the Lost Lamp.
- Jafar soon returned to get revenge on Pooh and the gang in Pooh's Adventures of Scooby-Doo and the Alien Invaders.
- The storyline continues in Winnie the Pooh and The Return of Jafar.
- The original version featured the end credits music from The Land Before Time (composed by the now-late James Horner) as the end credits music, which was used again as the end credits music for Pooh's Adventures of Osmosis Jones. However, the remake version uses the end credits version of Wherever You Are (performed by Barry Coffing and Vonda Shepard) from Pooh's Grand Adventure: The Search for Christopher Robin as the end credits song as reference to the elements of that film. Because of that, the end credits version of the song A Whole New World (performed by Peabo Bryson and Regina Belle) from the real film was instead used as the end credits song for both Winnie the Pooh Meets Cinderella (as the film involves romance) and will continue to be used as one of the end credits songs for the Pooh's Adventures of The Black Stallion triple feature (as those films feature the titular Arabic horse) and Pooh's Adventures of Scooby-Doo and the Ghoul School.