Winnie the Pooh and his friends have travelled back to New York City and meets Timmy Turner's long lost cusion; Jessie, a small town Texan teen who has come to New York to pursue her career as an actress. However, she ends up as a nanny for a high profile couples four children.
- The Vultures, Jiminy Cricket, Zazu, Ash Ketchum, Pikachu, Misty, Brock, Togepi, Littlefoot, Cera, Ducky, Petrie, Spike, Simba, Timon, Pumbaa, Timmy Turner, Cosmo and Wanda, Harry Potter, Ron Weasley, Hermione Granger, Genie, Alex, Marty, Gloria, Melman, Bugs Bunny, Daffy Duck, Baloo, Bagheera, King Louie, Tennessee Tuxedo, and Chumley will guest star in this series.
- Littlefoot, Harry Potter, Alex and their friends will meet Timmy Turner, Cosmo and Wanda for the first time.
- Jessie was released on Disney Channel in 2011 the same year both Winnie the Pooh and Harry Potter and the Deathly Hallows Part 2 were released in theaters and and air season 8 of The Fairly OddParnets air on Nickelodeon.
- Kronk, Zhane, Korra and her friends (from Daniel's Pooh's Adventures Team) are absent due to this being a past adventure.
- The Winnie the Pooh series, The Jungle Book, Pinocchio, The Lion King, Aladdin and Jessie were all made by Disney.
- In this series, it will reveal that Jessie is Timmy Turner's long lost older cousin.
- Like Pooh's Adventures of Austin & Ally, This series will take place during Daniel Esposito's Kingdom Heart crossover TV series Sora's Adventures of Mighty Morphin Power Rangers, and before PrinceJosh1992's Anniversary Special Sora's Adventure Special: The Adventure Continues. In which this series is known to be a past adventure.
- This series will continues in Winnie the Pooh is Bunk'D.