A Day in the Limelight: Nearly every supporting character gets at least two or three episodes where they are the main focus.
And Starring: When Paul Winchell was still a part of the series, he received the credit "And Paul Winchell as Tigger."
Baths Are Fun: "The Old SwitcheRoo," based on earlier material, has Tigger and co. trying to help get Roo out of taking a bath because baths are "the end." Piglet ends up getting used as a substitute for Roo and being bathed by Kanga. But when Tigger and Roo get covered in mud and gum, they both end up in the bath. "Scrubbly bubbly." Tigger is forced to admit that when you take a bath "You get... you get clean" and Roo declares "This is fun!" Tigger was right about one thing, though... it was The End. (And the episode ends.) These events were later adapted for Piglet's Big Movie and the Carly Simon song "Mother's Intuition."
Box And Stick Trap: An episode had Pooh trying to locate Rabbit's lost hammer, by using one of these and setting out a bunch of nails as bait. The trap gets set off and when Pooh goes over to see what he caught, he finds that he caught a saw instead.
Calling Card: The Pack Rats' gimmick of stealing things and leaving behind walnuts as "payment".
Calvinball: It is not at all clear what the point of the game that they are playing in "What's the Score, Pooh?" is, or what even the basics of the game are.
Cartoon Bug Sprayer: Sometime wielded by Rabbit in his battles with the bugs that invade his garden. He wants one for Christmas in "Winnie the Pooh and Christmas, Too".
Christmas Episode: "Winnie the Pooh and Christmas, Too". There were also special episodes for Halloween, Thanksgiving, New Year's Day, and Valentine's Day.
Continuity Nod: In "Friend in Need" Rabbit asks how Pooh got into his house with the door locked, Pooh responds that his back door was open, which is what he did in The Many Adventures of Winnie the Pooh. (Although the wooden door leading to the garden was the "back door" in that film.)
One episode says that Pooh is a pro at doing "nothing," a reference to the end of the film.
Clothing Damage: The back of Pooh's shirt gets torn off at the end of "Gone with the Wind".
Crazy Enough to Work: In "Things That Go Piglet in the Night," Tigger's plan to help Eeyore swing from the tree is to attach wooden wings and a parachute, and then launch him from another swing. Even Tigger is shocked that this works.
Cultural Translation: Moreso than the original: Christopher Robin now had an American accent and lived in what looked like a typical US suburb — albeit one that seems to use the British street-numbering system.
Darker and Edgier: Compared this one to the original featurettes, and more to the later movies and shows such as My Friends Tigger and Pooh this show has surprisingly many dark and scary moments, even if most of them have a distinct comical undertone. This is probably as Dark And Edgy as you'll ever see Winnie the Pooh.
Dark Reprise: "There's No Camp Like Home" opens with Piglet in a scary version of "Heffalumps and Woozles" from Blustery Day.
While not a Fairy Tale, the episode "The Monster Frankenpooh" is fractured storytelling as well.
Heel Face Turn: Nasty Jack in "Paw And Order" ends up becoming the sheriff.
I Just Want to Be You: Tigger tries to teach Eeyore how to be more cheerful. Eeyore interprets his lessons as "being just like Tigger", and soon he's painted himself in orange and black stripes and bouncing the others.
Insomnia Episode: The episode "Rock-A-Bye Pooh" had Piglet unable to go to sleep, due to a bad dream that he had where he lost his friends while they were going on a picnic. Pooh, Rabbit, and Tigger then work hard using different methods to try to get Piglet to go back to sleep, but to no success, until a storm blows up to which Piglet's dream does sort of come to reality. Fortunately for him, he's reunited with his friends in the end and he is able to sleep at night again.
Interacting With Shadow: In one episode, Piglet befriends his shadow when his friends were too busy with their own activities to play with him.
Jerk with a Heart of Gold: Most everyone agrees Rabbit's a jerk, but he has several moments throughout the series and features where he's clearly a softy and a good friend in the long run.
Joker Jury: The trial by balloons in "Balloonatics".
Lady Mondegreen: Used in-universe. Tigger's alter ego "The Masked Offender" (from a mishearing of "The Masked Avenger", the hero from a story Christopher Robin read to them).
Malaproper: Mostly Tigger, but occasionally other characters too, such as Pooh.
Tigger is the origin of this, at least in Winnie the Pooh. Heffalump, Woozle, Gabloon, Animule, anything except Jagular which Pooh came up with.
Never Say "Die": When Rabbit disappears in one of Gopher's many dynamite explosions and a search of the area fails to turn up any sign of hide nor bunny, Tigger states glumly, "We're just gonna have to face it! Bunny-Boy is gone." (He turns up immediately afterward hanging from a tree.
Ninja Pirate Zombie Robot: When you hear about "horse thieves", you'd expect thieves who steal horses instead of thieves who are horses.
Non Fatal Explosions: Gopher's dynamite causes plenty of property damage, but the characters emerge from the same explosions unharmed.
Noodle Incident: In The Bug Stops Here, Tigger, Rabbit, and Piglet go off to try and catch a bug. When Pooh and the others find them in a place set off with traps, the three of them are caught in a net suspended in the air, with no explanation of what happened.
Or My Name Isn't...: At least two episodes had Pooh say, "...or my name isn't Winnie the Pooh! Which it is..."
Out-of-Character Moment: In "The Piglet Who Would Be King", Rabbit is friendly with Tigger and enthusiastic of going on a journey with him and Piglet. Normally, he would try to keep himself out of these journeys, especially if Tigger's involved.
The Other Darrin: Halfway through the show's run, Jim Cummings, already voicing Pooh, replaced Paul Winchell as Tigger as well. (Winchell was very much still alive at that point and returned to voice Tigger in Pooh's Grand Adventure.)
Parrot Expo-what?: In Monkey See Monkey Do Better, Rabbit challenges toy ape Bruno to gardening.
Real After All: Prior to this series, Heffalumps and Woozles were merely creatures of Pooh and the others' imagination in both the original books and Disney features. Starting from New Adventures they begin appearing in person, usually as bumbling antagonists.
The Runt at the End: "The Piglet Who Would Be King" had a herd of heffalumps thunder past, followed by a tiny heffalump chanting "The land of milk and honey! The land of milk and honey! Hooray!"
Sanity Slippage: Rabbit, very quickly, when he first starts taking care of Kessie, giggling and making faces like maniac and babbling about having carrots to take care of. He snaps out of it before long, though.
Shout Out: In "Rabbit Takes a Holiday", the others manage to completely destroy Rabbit's home and garden while he's away, so they erect huge murals depicting them in pristine condition to try to fool him. Sound familiar?
Shown Their Work: Though more directly based on the Disney featurettes, occasional episodes make references to story material from the original A.A. Milne novels. In "The Big Switcheroo", for example, Tigger switches Piglet with Roo inside Kanga's pouch so Roo can avoid getting a bath (this story would again be adapted for part of Piglet's Big Movie), while in "Eeyore's Tail Tale" Owl mistakes Eeyore's tail for a door bell (this story would again also be adapted for part of the 2011 Winnie The Pooh film).
Stop Helping Me!: Eeyore went through this when everyone tried to cheer him up in "Donkey For A Day".
Superstition Episode: On one episode, Tigger breaks a mirror in Rabbit's home, and Rabbit tells him that means seven years bad luck. Tigger dismisses it, as it wasn't his mirror that broke, and he tries to help Rabbit avoid bad luck, which just results in Rabbit getting one misfortune after another. Eventually, it's revealed that the mirror belonged to Pooh, so Tigger tries to help him avoid bad luck, with the same results. Eventually, after everyone but Tigger suffers from bad luck, it become apparent that Tigger is the one who is unlucky, so he's cast out. The others feel sorry for him and reverse the bad luck by "fixing" the mirror (taping a picture of Tigger so that he thinks it's his reflection).
Surprise Party: In "Goodbye, Mr. Pooh," Winnie the Pooh's friends throw him one because they think he's moving away. Because of it, he actually does move away, but soon returns, only to find his house taken by Eeyore.
Survival Mantra: Subverted in "Knight for a Day" with Piglet chanting "I am not brave, I am not brave..."