Pooh's Adventures of Madagascar (originally uploaded as Winnie the Pooh Goes to Madagascar) is LionKingRulezAgain1's first Winnie the Pooh crossover that is not considered as Simba, Timon, and Pumbaa's Adventures film. It premiered on YouTube in September 2009. A remake version of the movie will be made by Daniel Esposito and appear on Google Drive in the near future.
Winnie the Pooh and his friends go to the Central Park Zoo to meet Alex, Marty, Gloria, and Melman, but one day later, they are sent from the zoo to the wild before they are dumped into Madagascar.
- The Vultures will guest star in the remake version of this film, since it turned out they were originally going to debut in this film before Daniel Esposito first cancelled it and gave the film to LionKingRulezAgain1 (Jonathan Oosterhof) due to copyright claims from DreamWorks.
- LionKingRulezAgain1's original version was a PAL film with PAL bits from The Many Adventures of Winnie the Pooh, Pooh's Grand Adventure: The Search for Christopher Robin, and The Tigger Movie and NTSC bits from Winnie the Pooh: A Very Merry Pooh Year and Pooh's Heffalump Movie. However, Daniel Esposito's upcoming remake version of the film will be an NTSC film with NTSC bits from the Winnie the Pooh films and The Jungle Book 1 and 2.
- This film was originally made and uploaded as Winnie the Pooh Goes to Madagascar, but five years later, it was discovered that the latest Madagascar spin-off TV series entitled All Hail King Julien would be a prequel to the Madagascar films and Daniel Esposito accepted Yru17's request to make a Winnie the Pooh crossover with that TV show as a prequel to the Winnie the Pooh/Madagascar films as well as remaking the first two Winnie the Pooh/Madagascar films (with the first film now marking the second time Pooh and his friends visit Madagascar and meet King Julien, Maurice, and Mort because they will first do so on Winnie the Pooh Says All Hail King Julien), so the upcoming remake version will now be titled Pooh's Adventures of Madagascar instead.
- The storyline continues in Pooh, Simba, Timon, and Pumbaa's Adventures of Madagascar: Escape 2 Africa, Pooh's Adventures of Madagascar 3: Europe's Most Wanted and Pooh's Adventures of Penguins of Madagascar.