The Ralph Caldecott Medal recognizes the artist of the most distinguished American picture book for children. It is awarded annually by the Association for Library Service to Children, a division of the American Library Association.
- 2013: This is Not My Hat by Jon Klassen
- 2012: A Ball for Daisy by Chris Raschka
- 2011: A Sick Day for Amos McGee by Philip Christian Stead, illustrated by Erin E. Stead
- 2010: The Lion and the Mouse by Jerry Pinkney
- 2009: The House in the Night written by Susan Marie Swanson, illustrated by Beth Krommes
- 2008: The Invention of Hugo Cabret by Brian Selznick
- 2007: Flotsam by David Wiesner
- 2006: The Hello, Goodbye Window written by Norton Juster, illustrated by Chris Raschka
- 2005: Kitten's First Full Moon by Kevin Henkes
- 2004: The Man Who Walked Between the Towers by Mordicai Gerstein
- 2003: My Friend Rabbit by Eric Rohmann
- 2002: The Three Pigs by David Wiesner
- 2001: So You Want to Be President? written by Judith St. George, illustrated by David Small
- 2000: Joseph Had a Little Overcoat by Simms Taback
- 1999: Snowflake Bentley written by Jacqueline Briggs Martin, illustrated by Mary Azarian
- 1998: Rapunzel by Paul O. Zelinsky
- 1997: Golem by David Wisniewski
- 1996: Officer Buckle and Gloria by Peggy Rathman
- 1995: Smoky Night written by Eve Bunting, illustrated by David Diaz
- 1994: Grandfather's Journey by Allen Say
- 1993: Mirette on the High Wire by Emily Arnold McCully
- 1992: Tuesday by David Wiesner
- 1991: Black and White by David Macaulay
- 1990: Lon Po Po: A Red-Riding Hood Story from China by Ed Young
- 1989: Song and Dance Man written by Karen Ackerman, illustrated by Stephen Gammell
- 1988: Owl Moon written by Jane Yolen, illustrated by John Schoenherr
- 1987: Hey, Al written by Arthur Yorink, illustrated by Richard Egielski
- 1986: The Polar Express by Chris Van Allsburg
- 1985: Saint George and the Dragon written by Margaret Hodges, illustrated by Trina Schart Hyman
- 1984: The Glorious Flight: Across the Channel with Louis Bleriot by Alice & Martin Provensen
- 1983: Shadow written by Blaise Cendrars, translated and illustrated by Marcia Brown
- 1982: Jumanji by Chris Van Allsburg
- 1981: Fables by Arnold Lobel
- 1980: Ox-Cart Man written by Donal Hall, illustrated by Barbara Cooney
- 1979: The Girl Who Loved Wild Horses by Paul Goble
- 1978: Noah's Ark by Peter Spier
- 1977: Ashanti to Zulu: African Traditions written by Margaret Musgrove, illustrated by Leo & Diane Dillon
- 1976: Why Mosquitoes Buzz in People's Ears written by Verna Aardema, illustrated by Leo & Diane Dillon
- 1975: Arrow to the Sun by Gerald McDermott
- 1974: Duffy and the Devil written by Harve Zemach, illustrated by Margot Zemach
- 1973: The Funny Little Woman written by Arlene Mosel, illustrated by Blair Lent
- 1972: One Fine Day by Nonny Hogrogian
- 1971: A Story A Story by Gail E. Haley
- 1970: Sylvester and the Magic Pebble by William Steig
- 1969: The Fool of the World and the Flying Ship written by Arthur Ransome, illustrated by Uri Shulevitz
- 1968: Drummer Hoff written by Barbara Emberley, illustrated by Ed Emberley
- 1967: Sam, Bangs & Moonshine by Evaline Ness
- 1966: Always Room for One More written by Sorche Nic Leodhas, illustrated by Nonny Hogrogian
- 1965: May I Bring a Friend? written by Beatrice Schenk de Regniers, illustrated by Beni Montresbyor
- 1964: Where the Wild Things Are,by Maurice Sendak
- 1963: The Snowy Day by Ezra Jack Keats
- 1962: Once a Mouse retold and illustrated by Marcia Brown
- 1961: Baboushka and the Three Kings by Ruth Robbins, illustrated by Nicolas Sidjakov
- 1960: Nine Days to Christmas written by Marie Hall Ets and Aurora Labastida, illustrated by Marie Hall Ets;
- 1959: Chanticleer and the Fox written by Barbara Cooney, illustrated by Barbara Cooney
- 1958: Time of Wonder by Robert McCloskey
- 1957: A Tree Is Nice written by Janice Udry, illustrated by Marc Simont
- 1956: Frog Went A-Courtin' written by John Langstaff, illustrated by Feodor Rojankovsk
- 1955: Cinderella, or the Little Glass Slipper translated from Charles Perrault by Marcia Brown, illustrated by Marcia Brown
- 1954: Madeline's Rescue by Ludwig Bemelmans
- 1953: The Biggest Bear by Lynd Ward
- 1952: Finders Keepers written by William Lipkind, illustrated by Nicholas Mordvinoff
- 1951: The Egg Tree by Katherine Milhous
- 1950: Song of the Swallows by Leo Politi
- 1949: The Big Snow by Berta & Elmer Hader
- 1948: White Snow, Bright Snow by Alvin Tressel, illustrated by Roger Duvoisin
- 1947: The Little Island written by Golden MacDonald, pseud. [Margaret Wise Brown], illustrated by Leonard Weisgard
- 1946: The Rooster Crows by Maud & Miska Petersham
- 1945: Prayer for a Child written by Rachel Field, illustrated by Elizabeth Orton Jones
- 1944: Many Moons written by James Thurber, illustrated by Louis Slobodkin
- 1943: The Little House by Virginia Lee Burton
- 1942: Make Way for Ducklings by Robert McCloskey
- 1941: They Were Strong and Good by Robert Lawson
- 1940: Abraham Lincoln by Ingri & Edgar Parin d'Aulaire
- 1939: Mei Li by Thomas Handforth
- 1938: Animals of the Bible, A Picture Book written by Helen Dean Fish, illustrated by Dorothy P. Lathrop