Winnie the Pooh and the Diary of a Wimpy Kid is another Winnie the Pooh crossover planned to be made by Yakko Warner and Shadow101815. It will appear on Google Drive in the near future.
The film starts when Rodrick wakes up his brother Greg, saying it was time for school. However, Rodrick tricked Greg, as it is already night. After the title sequence, Greg attends his first day at middle school and discovers the ups and downs, such as the missing stall doors in the boys' bathroom and the difficulties of obtaining a seat during lunch break. During P.E. lessons, he and his best friend Rowley escape from a game of Gladiator and learn about the Cheese Touch - a rotten piece of cheese on the basketball court that makes anyone who touches it an outcast. Greg also meets Angie, a girl who isolates herself from the other girls to survive. Greg states his intention of becoming the most popular student in school.
At the end of the day, Rowley unintentionally embarrasses both boys by asking Greg if he wants to come over and "play". Greg looks through Rodrick's yearbook at home and Rodrick catches them, threatening to kill Greg. The next day, Greg signs up for wrestling to become popular but suffers humiliating losses against both Fregley, a weird outcast, and Patty Farrell, Greg's arch-enemy from elementary school. On Halloween, the two boys encounter teenagers while trick or treating, and they are drenched with water. When Greg threatens to call the cops, the teenagers chase them to his Grandma's house. Some time later on, Greg makes it an effort to make Rowley popular by changing his style of clothing and looks, and how he wears a backpack.
The boys join Safety Patrol in an effort to become popular, and they try out for a contest that offers a student a chance to become the new cartoonist for the school paper. After Greg accidentally broke Rowley's arm during a game the boys played, Rowley becomes extremely popular, and wins the contest. Greg becomes jealous of him. At Safety Patrol, Greg panicks when he encounters a truck identical to the teenagers' from Halloween, and hides the kids in a construction zone. He is spotted by a neighbour who mistakes him for Rowley. To his own bewilderment, Rowley is banned from the Patrol, but Greg eventually confesses to Rowley; Rowley accuses Greg of being selfish and ends their friendship. Rowley makes friends with Collin who replaces Greg as Rowley's new best friend.
Greg decides to pursue popularity without Rowley by joining the school play. At tryouts, Greg's soprano voice earns him the role of Dorothy Gale; however, Patty threatens the teacher into casting her instead. Greg signs up as a tree, hoping to throw apples on Patty during the play, but during rehearsal, the trees are told they won't throw apples but sing a song instead. At the performance, Greg refuses to sing as Rodrick is videotaping the performance, and begins throwing apples, ending the play in chaos. Rodrick is grounded but Greg fails to reconcile with Rowley.
One day at school, Rowley and Greg confront each other. Patty and the other kids force Greg and Rowley to fight; however, neither of them are good at fighting. The Halloween teenagers arrive at the scene and force the school to flee, but catch Rowley and Greg. They force Rowley to eat the cheese before the P.E. teacher forces them to flee. When the other kids notice that the Cheese has been moved from its original location and has been bitten, Greg covers up for Rowley by saying he ate it. This mends their friendship but makes Greg an outcast, as he is thought to have the Cheese Touch.
When the yearbooks are published, he and Rowley make the Class Favorites page as "Cutest Friends."
- The 100 Acre Avatar League, The 100 Acre Wood Rebel Alliance, Ash and his friends, the Jungle Adventure Crew, Littlefoot, Cera, Ducky, Petrie, Spike, Chomper, Ruby, Guido, Grandpa Longneck, Grandma Longneck, Skip, Mr. Thicknose, Kion and his friends, SpongeBob and his friends, the Alfea Adventure Crew, Charlie Barkin, Itchy Itchiford, Sailor Moon and the Sailor Scouts, Tuxedo Mask, the McDonaldland Adventure Crew, The Simpsons, Santa's Little Helper, Snowball II, Grandpa Simpson, Patty and Selma, Gina Vendetti, Milhouse VanHouten, Alex Whitney, Darcy, Laura Powers, Ned Flanders, Todd Flanders, Rod Flanders, Peter Griffin and his family, Glenn Quagmire, Joe Swanson, Cleveland Brown and his family, Tim the Bear, Stan Smith and his family, the Futurama gang, Bob Belcher and his family, Fred Flintstone, Wilma Flintstone, Barney Rubble, Betty Rubble, Dino, George Jetson, Jane Jetson, Judy Jetson, Elroy Jetson, Astro, Ace Bunny and his friends, Godzilla and his friends, the Animaniacs gang, Belle and her friends, the Hogwarts Adventure Crew, Dylan (Shadow101815), The Latest Buzz gang, Max and his friends (from The Secret Life of Pets), Red and his friends (from The Angry Birds Movie), Basil of Baker Street, Dr. David Q. Dawson, PrinceJosh1992's Sora's Adventures team, Aqua, Terra, Ventus, Mickey Mouse, Pluto, Arlo and his family and friends (from The Good Dinosaur), Jesse Katsopolis and his family (from Full House), Lou and his friends (from Cats & Dogs), Princess Anna and her friends, The DigiDestined and their Digimon, Scooby-Doo and the gang, Scrappy-Doo, Scooby-Dum, Rex, Woog, Elsa, Dweeb, Fievel Mousekewitz and family and friends, Bron, Shorty, Ali, Hyp, Mutt, Nod, Mr. Thicknose, Pterano, Alex, Marty, Melman, Gloria, The Penguins of Madagascar, Princess Tiana, Prince Naveen, Ray the Firefly, Mama Odie, Taran, Princess Eilonwy, Fflewddur Fflam, Gurgi, Orddu, Orgoch, and Orwen, Aladdin, Princess Jasmine, Abu, Iago, Danny and Sawyer and their friends (from Cats Don't Dance), Ariel and her family, The Goonies, Jesse Greenwood, Elvis, Randolph Johnson, Nadine, Celebi, Baloo, Bagheera, King Louie, Napoleon, Birdo, Malcolm and his family, Artie, Pete, Eric, the Kids Next Door, Numbuh 362, Richie Cunningham and his friends, Ralphie Parker and his friends, Dr. Alan Grant and his friends (from Jurassic Park), The Muppets, the Ewoks, Toaster and his friends, Kenai, Koda, Mulan, Mushu, Cri-Kee, Aladar and his family, Chanticleer and his friends, the Oliver & Company gang, Rocko, Heffer, Filburt, the Rugrats, and The Wild Thornberrys will guest star in this film.
- Due to mild language and content, the words "crap", "crappy", "Turd Burglar", "wuss", and the profane use of "freaking" will be replaced with the words "crud", "cruddy", "Dirt Burglar", "wimp", and "stupidly", the uses of God's name in vain will be replaced with the word "gosh", and some violent images, rude humor, some disturbing images, a brief peeing bit, and some other content will all be censored to make this film more G-rated.
- Yakko Warner originally requested Yru17 to re-edit this film, which he accepted, but he eventually retired from re-editing anymore films (due to him aging), so Yakko Warner and Shadow101815 will make this film instead.
- The storyline continues in Winnie the Pooh and the Diary of a Wimpy Kid: Rodrick Rules, Winnie the Pooh and the Diary of a Wimpy Kid: Dog Days, Winnie the Pooh and the Diary of a Wimpy Kid: Class Clown (animated short film), and Winnie the Pooh and the Diary of a Wimpy Kid: The Long Haul.