Winnie the Pooh: Sing a Song with Pooh Bear is a video released as a VHS in 1999. It was later released as a DVD in April 2003, to coincide with the theatrical release of Piglet's Big Movie a renamed Sing a Song with Pooh Bear and Piglet Too.
- Winnie the Pooh
- Rumbly in My Tumbly (By Winnie the Pooh from Winnie the Pooh and the Honey Tree)
- The Wonderful Thing About Tiggers (By Tigger from Winnie the Pooh and the Blustery Day and Winnie the Pooh and Tigger Too)
- The Kangaroo Hop (By Kanga, Roo, Owl, Pooh and Tigger)
- Try A Little Something New & High & Low Medley (By Owl and Tigger)
- The One And Only One (By Piglet and Eeyore)
- The Floating Song (By Winnie the Pooh in Balloonatics from The New Adventures of Winnie the Pooh)
- Harvest What You Grow (By Rabbit)
- Heffalumps and Woozles (By Honey Pots from Winnie the Pooh and the Blustery Day)
- Nothing's Too Good for a Friend (By Tigger and Rabbit from The Piglet Who Would Be King from The New Adventures of Winnie the Pooh)
- My Song (By Pooh and friends)
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