In the PC/Mac version, which is a point-and-click adventure, Piglet goes around collecting ingredients for a soup.
On the first day of autumn in the Hundred Acre Wood, Piglet is observing his friends go about their lives and have several problems, such as Pooh trying to get honey, Roo trying to get his ball down from a tree, Owl trying to find his missing memory book, and so forth. When Piglet spots a strange shadow called the "Granosaurus", no one believes him. When he tells Christopher Robin about what he saw, he tells him he must believe in himself and face his fears. Believing he isn't any of that, Piglet leaves the wood just as his friends begin to fall asleep. Piglet soon discovers a mysterious telescope that allows him to enter the dreams of his friends and help them with their problems, learning how to be as brave as he can be.
The object of the game is to travel into each of Piglet's friends' dreams and help complete an objective each character is trying to accomplish, similar to their real world problem. Throughout the game, Piglet must face various Heffalumps and Woozles scattered throughout the dream worlds by scaring them with "brave faces", otherwise the creatures will scare Piglet and cause him to worry and panic. Piglet must also search for cookies hidden throughout the level which can be used to purchase new brave faces at the "Brave Face Factory", which are needed in order to finish the game. Tigger and Pooh are also played with in specific levels of the game; Tigger must sneak quietly past the Heffalumps and Woozles, and Pooh must run away after the rumbling from his tummy attracts them.
Two years later, the game received a Spiritual Successor called Winnie the Pooh's Rumbly Tumbly Adventure, which puts the focus on Pooh Bear himself as he revisits his friends' birthdays, with the gameplay more-or-less identical to its predecessor with the addition of Eeyore as a playable character.
This game provides examples of:
- Artistic License: It is raining perpetually in Eeyore's dream, yet Roo is carrying a candle lamp. Wouldn't the water from the rain extinguished the lamp? Then again, it is a dream...
- Always Night: It is endlessly nighttime in Owl and Eeyore's dream worlds.
- Art Shift: Roo's dream consists of a mostly cardboard playbox world.
- Amusement Park: What serves as the central attraction of the fall area in Tigger's dream.
- Battle Theme Music: The Grimace Mode theme, which plays as the player helps Piglet scare the creature.
- Bigger on the Inside: In Eeyore's dream, Eeyore's stick house manages to fit an entire castle under the ground.
- Bleak Level: Eeyore's dream takes place in an endless rainy night world with a drab medieval castle underground, to reflect his gloomy persona. Roo even lampshades it.
- Blowing a Raspberry: Piglet's first and default brave face, which is also the weakest.
- Bonus Stage: "Bravest of them All". After Piglet successfully completes a dream, the dream is unlocked and the Heffalumps and Woozles are afraid of Piglet now, and the player has to help Piglet catch up with the enemies before the time runs out.
- Chekhov's Gun: In Eeyore's dream, the lamp Roo carried at the beginning of the level becomes useful near the end when the power in the castle goes out.
- Color Wash: Some brave faces will bathe Piglet in a colored glow as he scares the beast. He is bathed in green light when he tugs his lips wide open and says "Ueeehhhh!", and he gets a red lighting when he pretends to be some sort of monster complete with a charging position and angry face.
- Dream Walker: The game revolves around Piglet traveling into his friends' dreams.
- Easy Amnesia: Owl's dream has Owl literally lose his memory when his memory book goes missing.
- Expressive Health Bar: Not the case of an actual health bar, but Piglet's courage is based on how he moves. When normal, he walks generically; after one scare when worried, he scampers slightly while clasping his hands; and after two scares when he begins to panic, he runs frantically. It's even reflected in the loading screen as well.
- Final Boss: The Granosaurus which Piglet must scare off to save his friends...though it's just a bunch of leaves being blown about by the wind.
- Fisher King: The themes of the various dream worlds reflect the personalities of whoever is dreaming.
- Forest of Perpetual Autumn: The fall area of Tigger's dream, which often has leaves blocking Piglet's path.
- Four-Seasons Level: Tigger's dream is made up of four different regions representing the four seasons; summer is a vast wood where the trees all have Tigger stripes, fall is a carnival, winter is a snowy mountain with an ice cave, and spring is a normal generic forest.
- Gotta Catch 'Em All: Piglet must collect all the brave faces in order to finish the game.
- Great Big Library of Everything: Owl's dream is this, consisting of various books and reading equipment, making it resemble an endless library.
- Growling Gut: Pooh as usual; but in parts of the game where he takes over the gameplay, it ends up attracting a myriad of Heffalumps and Woozles and he must run away before they catch up to him.
- Halfway Plot Switch: Roo's dream begins with Kanga asking Piglet to find Roo, who locked himself in his playroom and lost the key. After the door was unlocked, it changes to Piglet helping Roo get his ball down from the clouds.
- Help, I'm Stuck!:
- Early on in Pooh's dream, Pooh gets stuck in some caramel.
- When first encountering Roo in his dream, he has locked himself in his playroom and lost the key.
- In Rabbit's dream, Rabbit gets stuck in the dirt of his garden.
- Interface Screw: Starting in Roo's Dream, Piglet begins encountering Heffalumps and Woozles who affect the button combinations in different ways such as Slot Machine Heffalumps who can change the buttons to press while the player still needs to hit the right combination of buttons.
- Mickey Mousing: Tigger's sneaking is accompanied by a musical plucking noise for every step taken.
- Musical Spoiler: When Piglet enters the room of a potentially dangerous enemy, a sneaky and foreboding track
replaces the regular background score. - Level Ate:
- Pooh's dream is full of various candies, cookies and desserts, to reflect his status as a Big Eater.
- Rabbit's dream is loaded with carrots.
- Marathon Level: Tigger's dream, the last dream before the final level, is the longest level in the entire game, taking at least an hour and a half to complete.
- Out of Focus: Kanga only appears in Roo's dream and has a brief appearance in the prologue, and was the only character not seen in the ending scene and the only one Piglet didn't have to rescue.
- Password Save: The GBA version uses this type of method unlike the home console versions.
- Playable Menu: Piglet can be moved around three hub areas to start a new game or load a saved game, approach the telescope to enter his friends' dreams, change game options, or peek at extras such as specific cutscenes and clips from Piglet's Big Movie.
- Race Against the Clock: In Grimace Mode, the player has to complete all the button sequences and help Piglet scare the creature before it reaches Piglet and scares him. The countdown timer isn't a clock, it's the Heffalump or Woozle walking towards Piglet, and once it gets close to him, time's up.
- Real After All: The "Blustery Day" level has the Heffalumps and Woozles appearing in the real world and Piglet has to save his friends from them. Averted with the "Granosaurus" which is just a bunch of leaves that look like a monster thanks to their shadows.
- Rule of Three:
- Enemies in The Very Definitely Final Dungeon usually require three grimace codes in order to be scared; also, three enemies need to be faced in said area.
- If Piglet gets totally scared (three times in a row, a third after panic mode), he will run back to the first room and start over.
- Sealed Evil in a Can: Once an enemy is fully scared, they will shrink and turn into a glowing flask for Piglet to collect. If Piglet does not collect said flask before leaving the area, the enemy will escape.
- Screw This, I'm Outta Here: If Piglet gets scared too much and becomes totally panicked, he is forced to run back to the first room and start over. Also when playing as Tigger or Pooh, if an enemy catches up with them, they are forced to run away and start over as well.
- Spectacular Spinning: The second-to-last brave face that Piglet learns has him spin around while twisting his body and saying "Blahhhh!". The background even spins with him.
- Starter Villain: The first Heffalump Piglet faces in the game, upon entering Rabbit's house in Pooh's dream.
- Stealth-Based Mission: Tigger's sections in Roo and Rabbit's dreams has him sneaking past Heffalumps and Woozles to help Piglet progress.
- Swapped Roles: The "Bravest of them All" bonus levels switches the roles of Piglet and the enemies, with the enemies now running away while Piglet has to catch them.
- Timed Mission:
- The Grimace Mode, as explained above. Piglet has to complete the grimace code and put on a very brave face to scare the Heffalumps and Woozles before they reach Piglet and scare him.
- For the "Bravest of them All" bonus level, Piglet has to catch all the runaway enemies before the timer runs out. There is no penalty for any enemy missed.
- The Very Definitely Final Dungeon:
- All the even-numbered dreams end with Piglet entering a dungeon-like area where he must scare three tough creatures in order to finish the level. Before proceeding, he must scare the talking door guarding the dungeon, which can only be done if he has collected all the brave faces up to now.
- The "Blustery Day" level serves as the final level of the whole game, where Piglet must rescue his friends from the Heffalumps and Woozles before taking on the "Granosaurus" from the prologue.
- Toy Time: Roo's dream resembles that of some sort of playroom, complete with doodles, sketches, and things made out of paper or cardboard.
- Variable Mix: The music for the Brave Face Factory gains more prominent horns as Piglet learns more brave faces.
