Winnie The Pooh meets The Fearless Four is the last film created by Legoland1085, as he Retired from making Winnie the Pooh crossovers.
When Buster the dog, Sawyer's sister Gwendolyn the cat, Tortellini the rooster and Fred the donkey are scheduled to be sent to a factory from which no animals ever return, they flee with Winnie the Pooh and his firends and make their way to the town of Bremen to try their luck as a singing group. But the city has a law against music, and soon, they've run afoul of the tyrant who controls the town while their old friends Timmy, Jenny, Matt, and Metalgarurumon are on the quest to save the animals and destroy the factory. This animated musical adventure stars the vocal talents of B.B. King, James Ingram and Oleta Adams.
- It is a PAL movie with NTSC bits from Pooh's Heffalump Movie, Piglet's Big Movie, Cats Don't Dance and the Thomas the Tank Engine episodes.
- It will also be an uncut German/English Film in which when they speak to Pooh and friends, they speak English and when they don't speak to Pooh and Friends, they speak in their natural language. However, most of this film use the English dub of The Fearless Four.
- Danny, Sawyer, Dave Felis, Renamon, Gaomon, Billy, Timmy, Jenny, Thomas the Tank Engine, Matt, MetalGarurumon and Darla Dimple guest star in this film.
- This film reveals that Gwendolyn is the sister of Sawyer.