Ash's Adventures of Christopher Robin is another upcoming Pokemon/Winnie the Pooh crossover planned to be made by Daniel Esposito, David Graham, and Shadow101815. It is a sequel to all of Daniel Esposito's Pokemon/Winnie the Pooh crossovers and Shadow101815's Harry Potter/Winnie the Pooh crossovers. It will appear on Google Drive in the near future.
Christopher Robin is leaving for boarding school, so his friends from the Hundred Acre Wood – Winnie the Pooh, Tigger, Piglet, Eeyore, Kanga, Roo, Owl, and Rabbit – throw him a goodbye party. In their usual meeting spot, Christopher comforts Pooh and tells him that he would never forget him. Despite this, his experiences in boarding school and the death of his father force him to mature quickly.
Robin subsequently goes to boarding school, grows up, meets and marries architect Evelyn, with whom he has a daughter named Madeline, and serves in the British Army in World War II. Upon returning, he finds a job as an efficiency expert at Winslow Luggages. He neglects his family due to his demanding job and plans on sending Madeline to boarding school. With his company hitting hard times, his superior, Giles Winslow Jr., tells him to decrease expenditures by 20%, largely by choosing which employees to lay off, and to present the necessary paperwork on Monday. This forces Christopher to forego his plan of traveling with his family to his countryside cottage in Sussex for the weekend before the summer ends. He reluctantly tells his family of the news; Evelyn and Madeline depart the next morning.
Meanwhile, Pooh awakens and is unable to find his friends, so he decides to travel through Christopher's door and finds himself in London, outside Christopher's house. He reunites with Christopher, who is shocked to see Pooh and reluctantly agrees to bring him back to the Hundred Acre Wood through his door near his Sussex cottage.
After sneaking past Christopher's family, the two enter the Hundred Acre Wood. Christopher becomes exasperated by Pooh's absent-mindedness and fear of Heffalumps and Woozles. This leads Christopher to get upset with Pooh about his usual antics; Christopher then tells Pooh that he's not a kid anymore. The two get separated in the fog. Christopher discovers Eeyore and Piglet, who lead him to the others hiding in a log out of fear of a Heffalump. Unable to persuade his friends that he is truly Christopher Robin, as they believe he's a Heffalump, he pretends to defeat a Heffalump to convince them with Eeyore's help. Everyone comes out of hiding when they realize that he is Christopher Robin all grown up, as everyone gathers over to him with joy in seeing him again. They all reunite with Pooh at their meeting spot. Christopher apologizes to Pooh for getting upset with him before; he assures Pooh that he's a bear with a big heart, and then gives him a big hug. The next morning, Christopher, who realizes that he fell asleep, leaves the Hundred Acre Wood so he won't miss his presentation. He encounters his family and, unable to tell them about the Hundred Acre Wood, quickly leaves.
Pooh realizes that Tigger has removed Christopher's paperwork in drying his briefcase, so Pooh, Tigger, Piglet and Eeyore decide to travel to London to give it back. They meet Madeline, who recognizes them from her father's drawings. She decides to join them in traveling to London so she can persuade her father not to send her to boarding school; Evelyn goes after her when she discovers Madeline's letter.
Christopher is about to present his plan, but realizes that his briefcase is filled with items given by Tigger. He is rushed out by Evelyn, and the two search London for Madeline. Madeline's group stow away in Winslow's company crates, but Tigger, Eeyore and Piglet are accidentally thrown out, and they encounter Christopher and Evelyn in the process. Madeline and Pooh arrive near the Winslow building, but the paperwork is blown away by the wind before they are reunited with Christopher's group. Christopher comforts his daughter and assures her of her importance to him and that she doesn't need to go to boarding school.
Christopher improvises a new plan involving reducing the prices of luggage, giving employees paid leave, and selling their luggage to everyday people to increase demand, instead of laying off employees. Winslow Jr. dismisses the idea, but his father Winslow Sr. warms up to it. Christopher points out Winslow Jr. hasn't been doing his part in helping with the plan, having been golfing all weekend, and Winslow Jr. is humiliated. Winslow Sr. agrees to the plan, and Christopher decides to spend time off with his family.
The Robins visit the Hundred Acre Wood and meet the rest of Christopher's friends. Christopher and Pooh share a tender moment overlooking the sunset.
In a mid-credits scene, the employees of Winslow's are seen having fun at the beach while Richard M. Sherman performs "Busy Doing Nothing" on a piano. The camera pans to Pooh and his friends relaxing on beach chairs with Eeyore saying "Thanks for noticing".
- The 100 Acre Avatar League, The 100 Acre Wood Rebel Alliance, Harry Potter, Ron Weasley, Hermione Granger, Rafiki, Tracey Sketchit, Devon and Cornwall, Olaf, The Seven Dwarfs, Green Arrow (Oliver "Ollie" Queen), Felicity Smoak, John Diggle, Wild Arms, Whizzer, Merlin, Rey, Finn, Poe Dameron, Rose Tico, BB-8, Emma Swan, Killian Jones, and The Reluctant Dragon will guest star in this film.
- The Jungle Book, Pinocchio, The Lion King, The Emperor's New Groove, The Nightmare Before Christmas, Star Wars Rebels, Frozen, The Rescuers Down Under, Aladdin, Snow White and the Seven Dwarfs, The Sword in the Stone, Star Wars: The Force Awakens, Star Wars: The Last Jedi, Once Upon a Time, The Reluctant Dragon, and Christopher Robin are all made by Disney.
- This is the first project to be made by Daniel Esposito, David Graham, and Shadow101815 altogether.
- This film will feature Kenny Loggins and Jim Messina's song House at Pooh Corner.
- Due to brief language, one of Christopher Robin's workers will exclaim either "My word" or "Dear gosh" instead of using Lord's name in vain in this film.