When Pooh floats down to land in the Hundred Acre Wood in Disney's Ready for Math With Pooh, he comes to earth in what will become a garden as the game progresses. The player signs in on a wheelbarrow and chooses a path from the three directions given - in each of these places he'll meet Pooh's friends; Piglet, Owl, Tigger, Eeyore, Roo, and Pooh himself, and play games designed to exercise his math skills at one of three levels.

Gameplay is identical to that of the sister game Disney's Ready to Read with Pooh: pointing and clicking the mouse will perform actions, the cursor is a little bumblebee that flutters it's wings whenever it is over a hotspot, and when dragging an object is necessary the game utilizes click-and-stick.