Madeline is forced to study by her father so she can go to a boarding school like he did. She goes to Sussex for the weekend. While studying, her mother tells her to go outside and play. While imitating a Wimbeldon match she meets Winnie the Pooh and his friends. When Christopher Robin leaves Sussex Tigger takes his important papers, leading Madeline to London. Eventually, she loses all his papers except one. Christopher Robin realizes that this was the only one he needed. He makes the decision to send Madeline to public school.