This medal is to be given to the artist who had created the most distinguished picture book of the year and named in honor of the nineteenth-century English illustrator Randolph J. Caldecott.
2007: The Invention of Hugo Cabret by Brian Selznick2006: Hello Goodbye Window by Juster Norton
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? by Judith St. George
2000: Joseph had a Little Overcoat by Simms Taback
1999: Snowflake Bentley by Jacqueline Briggs Martin
1998: Rapunzel by Paul O. Zelinsky
1997: Golem by David Wisniewski
1996: Officer Buckle and Gloria by Peggy Rathmann
1995: Smoky Night by Eve Bunting
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 by Karen Ackerman
1988: Owl Moon by Jane Yolen
1987: Hey, Al by Arthur Yorinks
1986: The Polar Express by Chris Van Allsburg
1985: Saint George and the Dragon by Margaret Hodges
1984: The Glorious Flight: Across the Channel with Louis Bleriot by Alice & Martin Provensen
1983: Shadow by Blaise Cendrars
1982: Jumanji by Chris Van Allsburg
1981: Fables by Arnold Lobel
1980: Ox-Cart Man by Donald Hall
1979: The Girl Who Loved Wild Horses by Paul Goble
1978: Noah's Ark by Peter Spier
1977: Ashanti to Zulu: African Traditions by Margaret Musgrove
1976: Why Mosquitoes Buzz in People's Ears by Verna Aardema
1975: Arrow to the Sun by Gerald McDermott
1974: Duffy and the Devil by Harve Zemach
1973: The Funny Little Woman by Arlene Mosel
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 by Arthur Ransome
1968: Drummer Hoff by Barbara Emberley
1967: Sam, Bangs & Moonshine by Evaline Ness
1966: Always Room for One More by Sorche Nic Leodhas, pseud. [Leclair Alger]
1965: May I Bring a Friend? by Beatrice Schenk de Regniers
1964: Where the Wild Things Are by Maurice Sendak
1963: The Snowy Day by Ezra Jack Keats
1962: Once a Mouse by Marcia Brown
1961: Baboushka and the Three Kings by Ruth Robbins
1960: Nine Days to Christmas by Marie Hall Ets and Aurora Labastida
1959: Chanticleer and the Fox by Barbara Cooney
1958: Time of Wonder by Robert McCloskey
1957: A Tree Is Nice by Janice Udry
1956: Frog Went A-Courtin' by John Langstaff
1955: Cinderella, or the Little Glass Slipper by Marcia Brown
1954: Madeline's Rescue by Ludwig Bemelmans
1953: The Biggest Bear by Lynd Ward
1952: Finders Keepers by Will, pseud. [William Lipkind]
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 byAlvin Tresselt
1947: The Little Island by Golden MacDonald, pseud. [Margaret Wise Brown]
1946: The Rooster Crows by Maude & Miska Petersham
1945: Prayer for a Child by Rachel Field
1944: Many Moons by James Thurber
1943: The Little House by Virginia Lee Burton
1942: Make Way for Ducklings by Robert McCloskey
1941: They Were Strong and Good
1940: Abraham Lincoln by Ingri & Edgar Parin d'Aulaire
1939: Mei Li by Thomas Handforth
1938: Animals of the Bible, A Picture Book by Helen Dean Fish