| 100% | HONEYPOT | 8 | Winnie the Pooh loves this jar and its content |
| 52% | HONEY | 5 | Bees make it and Winnie the Pooh loves it |
| 39% | BLUSTERY | 8 | Winnie the Pooh and the __ Day, 1968 Oscar winner |
| 38% | ACRE | 4 | Hundred ___ Wood (home to Winnie the Pooh and friends) |
| 35% | TOO | 3 | "Winnie the Pooh and Tigger ___" |
| 33% | HONEYPOT | 8 | Winnie the pooh treasure |
| 33% | MILNE | 5 | Winnie the Pooh creator |
| 32% | MILNE | 5 | Winnie the Pooh's creator |
| 32% | HONEY | 5 | Winnie the pooh's favorite |
| 32% | YOURS | 5 | (6/6) End the letter warmly with this word that goes along with "loving," and then sign your name below it |
| 32% | THATSMYJAM | 10 | “I love this song!” . . . or a hint to the starts of 17-, 27-, 39-, and 52-Across |
| 32% | ROO | 3 | Winnie the Pooh's young friend |
| 32% | TIGGER | 6 | Winnie the Pooh's bouncy friend |
| 32% | EEYORE | 6 | Winnie the Pooh's donkey friend |
| 32% | OWL | 3 | Winnie the Pooh's bird friend |
| 32% | ROO | 3 | Winnie the Pooh's joey friend |
| 32% | ROO | 3 | Winnie the Pooh's marsupial friend |
| 31% | ROO | 3 | Winnie the Pooh's young marsupial friend |
| 31% | BEAR | 4 | Winnie the Pooh or Smokey, for example |
| 31% | EEYORE | 6 | Winnie the Pooh's gloomy donkey friend |
| 31% | TIGGER | 6 | Winnie the Pooh's big cat friend |
| 31% | ROO | 3 | Winnie the Pooh's small hopping friend |
| 31% | ROO | 3 | Winnie the Pooh's young hopping friend |
| 31% | INS | 3 | "You have to know the ___ and outs of this machine to use it properly." |
| 31% | OWL | 3 | Winnie the Pooh's friend who can fly |
| 31% | TIGGER | 6 | Winnie the Pooh's orange-striped tiger friend |
| 31% | ROO | 3 | Marsupial friend of Winnie the Pooh |
| 31% | HONEY | 5 | Sweet treat for Winnie the Pooh |
| 31% | ROO | 3 | Joey in Winnie the Pooh stories |
| 31% | OWL | 3 | Wise friend of Winnie the Pooh |