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The Caldecott Medal is awarded annually to the illustrator - not the author - of the winning title. |
| Therefore, both illustrator and author are included in the list. |
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If the author column is blank, then the illustrator also was the author. |
| Year | Illustrator | Title | Author |
| 1938 | Lathrop, Dorothy P. | Animals of the Bible: A Picture Book | Fish, Helen Dean |
| 1939 | Handforth, Thomas | Mei Li | |
| 1940 | d'Aulaire, Ingri & Parin | Abraham Lincoln | |
| 1941 | Lawson, Robert | They Were Strong and Good | |
| 1942 | McCloskey, Robert | Make Way for Ducklings | |
| 1943 | Burton, Virginia Lee | Little House | |
| 1944 | Slobodkin, Louis | Many Moons | Thurber, James |
| 1945 | Jones, Elizabeth Orton | Prayer for a Child | Field, Rachel |
| 1946 | Petersham, Maude & Miska | Rooster Crows | |
| 1947 | Wiesgard, Leonard | Little Island | Brown, Margaret |
| 1948 | Duvoisin, Roger | White Snow, Bright Snow | Tresselt, Alvin |
| 1949 | Hader, Berta & Elmer | Big Snow | |
| 1950 | Politi, Leo | Song of the Swallows | |
| 1951 | Milhouse, Katherine | Egg Tree | |
| 1952 | Moordvinoff, Nicholas | Finders Keepers | Lipkind, William |
| 1953 | Ward, Lynd | Biggest Bear | |
| 1954 | Bemelmans, Ludwig | Madeline's Rescue | |
| 1955 | Brown, Marcia | Cinderella, or the Little Glass Slipper | Perrault, Charles |
| 1956 | Rojankovsky, Feodor | Frog Went A-Courtin' | Langstaff, John |
| 1957 | Simont, Marc | A Tree is Nice | Udry, Janice |
| 1958 | McCloskey, Robert | Time of Wonder | |
| 1959 | Cooney, Barbara | Chanticleer and the Fox | |
| 1960 | Ets, Marie Hall | Nine Days to Christmas | |
| 1961 | Sidjakov, Nicolas | Baboushka and the Three Kings | Robbins, Ruth |
| 1962 | Brown, Marcia | Once a Mouse | |
| 1963 | Keats, Ezra Jack | Snowy Day | |
| 1964 | Sendak, Maurice | Where the Wild Things Are | |
| 1965 | Montresor, Beni | May I Bring a Friend? | de Regniers, B. |
| 1966 | Nogrogian, Nonny | Always Room for One More | Alger, Leclair |
| 1967 | Ness, Evaline | Sam, Bangs & Moonshine | |
| 1968 | Emberley, Ed | Drummer Hoff | Emberley, B. |
| 1969 | Shulevitz, Uri | Fool of the World and the Flying Ship | Ransome, Arthur |
| 1970 | Steig, William | Sylvester and the Magic Pebble | |
| 1971 | Haley, Gail E. | A Story, A Story | |
| 1972 | Hogrogian, Nonny | One Fine Day | |
| 1973 | Lent, Blair | Funny Little Woman | Mosel, Arlene |
| 1974 | Zemach, Margot | Duffy and the Devil | Zemach, Harve |
| 1975 | McDermott, Gerald | Arrow to the Sun | |
| 1976 | Dillon, Diane & Leo | Why Mosquitoes Buzz in People's Ears | Aardema, Verna |
| 1977 | Dillon, Diane & Leo | Ashanti to Zulu: African Traditions | Musgrove, M. |
| 1978 | Spier, Peter | Noah's Ark | |
| 1979 | Goble, Paul | Girl Who Loved Wild Horses | |
| 1980 | Cooney, Barbara | Ox-Cart Man | Hall, Donald |
| 1981 | Lobel, Arnold | Fables | |
| 1982 | VanAllsburg, Chris | Jumanji | |
| 1983 | Brown, Marcia | Shadow | |
| 1984 | Provensen, Alice & Martin | Glorious Flight: Across the Channel with Louis Berliot | |
| 1985 | Hyman, Trina Schart | Saint George and the Dragon | Hodges, M. |
| 1986 | VanAllsburg, Christ | Polar Express | |
| 1987 | Egielski, Richard | Hey, Al | Yorinks, Arthur |
| 1988 | Schoenherr, John | Owl Moon | Yolen, Jane |
| 1989 | Gammell, Stephen | Song and Dance Man | Ackerman, Karen |
| 1990 | Young, Ed | Lon Po Po: A Red-Riding Hood Story from China | |
| 1991 | Macauley, David | Black and White | |
| 1992 | Wiesner, David | Tuesday | |
| 1993 | McCully, Emily Arnold | Mirette on the High Wire | |
| 1994 | Say, Allen | Grandfather's Journey | Lorraine, Walter |
| 1995 | Diaz, David | Smoky Night | Bunting, Eve |
| 1996 | Rathmann, Peggy | Officer Buckle and Gloria | |
| 1997 | Wisniewski, David | Golem | |
| 1998 | Zelinsky, Paul | Rapunzel | |
| 1999 | Azarian, Mary | Snowflake Bentley | Martin, J. |
| 2000 | Taback, Simms | Joseph Had a Little Overcoat | |
| 2001 | Small, David | So You Want to Be President? | St. George, J. |
| 2002 | Wiesner, David | Three Pigs | |
| 2003 | Rohmann, Eric | My Friend Rabbit | |
| 2004 | Gerstein, Mordicai | Man Who Walked Between the Towers | |
| 2005 | Henkes, Kevin | Kitten's First Full Moon | |
| 2006 | Raschka, Chris | Hello, Goodbye Window | |
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