The Young Artist Award is an annual award presented by the Young Artist Foundation. Started in 1980 by long-standing Hollywood Foreign Press member Maureen Dragone, the awards were envisioned specifically as awards to be presented to talented young people in television and movies who might otherwise be overshadowed by their older co-stars. Given that Winnie the Pooh is marketed for younger audiences, the shows generally have multiple stars and co-stars that are children.
They have been four nominations and zero wins.
Tim Hoskins was nominated for "Best Young Actor-Voiceover Role" for playing Christopher Robin in The New Adventures of Winnie the Pooh. He lost to Max Meier, for playing the title character in Kissyfur.
Pooh's Heffalump Movie
Pooh's Heffalump Movie was nominated for "Best Family Feature Film - Animation" during the 27th Annual Young Artist Awards, however it lost to Wallace & Gromit In The Curse Of The Were-Rabbit.
Chloe Grace Moretz
Chloe Moretz is the first, and only, person in the Pooh franchise to be nominated for more than one Young Artist Award. She was first nominated in 2008 for My Friends Tigger & Pooh and again in 2009 for "Hundred Acre Wood Haunt," a My Friends Tigger & Pooh DVD release.