Winnie the Pooh Goes to Madagascar is LionKingRulezAgain'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.
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.
- This film was originally supposed to be created by DisneyDaniel93, but he canceled it, due to copyright claims from DreamWorks, and replaced it with Winnie the Pooh Goes to Atlantis: The Lost Empire, so LionKingRulezAgain decided to make the film instead.
- This film was originally supposed to be an NTSC film (which DisneyDaniel93 uses), but ended up being a PAL film (which LionKingRulezAgain currently uses) due to LionKingRulezAgain making the film.
- 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, and The Tigger Movie and NTSC bits from Winnie the Pooh: A Very Merry Pooh Year and Pooh's Heffalump Movie.