Littlefoot and his friends (along with The Vultures, Jiminy Cricket, Zazu, Kronk, Zhane, Alex, Marty, Melman, Gloria, The Penguins of Madagascar, Jack Skellington, Baloo, and Bagheera) time-travel to the Hundred Acre Wood to reunite with Winnie the Pooh, Piglet, Tigger, Rabbit, and Eeyore as they help them find Christopher Robin in a place called Skull.
- The Vultures (Buzzie, Flaps, Dizzy, and Ziggy), Jiminy Cricket, Zazu, Kronk, Zhane, Alex, Marty, Melman, Gloria, The Penguins of Madagascar (Skipper, Kolwalski, Rico, and Private), Jack Skellington, Baloo, and Bagheera guest star in this film.
- This is one of The Land Before Time/Winnie the Pooh crossover films that actually takes place after the entire Winnie the Pooh/Land Before Time series (including the TV series), which explains Pooh and his friends already knowing Littlefoot and his friends.
- This is the only Land Before Time/Winnie the Pooh film to guest star The Vultures, Jiminy Cricket, Zazu, Kronk, and Zhane altogether due to these characters guest starring in Simba, Timon, and Pumbaa's Adventures of Piglet's Big Movie and most of the Pokemon/Winnie the Pooh films. However, Kronk and Zhane will also guest star in Littlefoot's Adventures of Pooh's Heffalump Movie.
- Like SpongeBob and Pooh's Grand Adventure: The Search for Christopher Robin, this is an NTSC film with NTSC bits from The Land Before Time films, The Jungle Book 1 and 2, Pinocchio, Mickey's Christmas Carol, The Lion King films, The Emperor's New Groove, Kronk's New Groove, the Madagascar films, and The Nightmare Before Christmas.