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Award Years for Chesley Award
| 1980's: | - | - | - | - | 1984 | - | 1986 | 1987 | 1988 | 1989 |
| 1990's: | 1990 | 1991 | 1992 | 1993 | 1994 | 1995 | 1996 | 1997 | 1998 | 1999 |
| 2000's: | 2000 | 2001 | 2002 | 2003 | 2004 | 2005 | 2006 | 2007 | 2008 | 2009 |
| 2010's: | 2010 | - | - | - | - | - | - | - | - | - |
| Best Cover Illustration - Hardcover | ||
| * | Cover (Forests of the Heart by Charles de Lint) | John Jude Palencar |
| Cover (The Tower at Stony Wood by Patricia A. Mckillip) | Kinuko Y. Craft | |
| Cover (Darkness Descending by Harry Turtledove) | Bob Eggleton | |
| Cover (The Lord of the Rings by J. R. R. Tolkien) | Donato Giancola | |
| Cover (Tangled Up in Blue by Joan D. Vinge) | Michael Whelan | |
| Best Cover Illustration - Paperback | ||
| * | Cover (Circle at Center by Douglas Niles) | Jean Pierre Targete |
| Cover (The Chick is in the Mail by Martin H. Greenberg & Esther Friesner) | Larry Elmore | |
| Cover (The Book of Ash #2: Carthage Ascendant by Mary Gentle) | Donato Giancola | |
| Cover (The Magic Dead by Peter Garrison) | Don Maitz | |
| Cover (The Clandestine Circle by Mary H. Herbert) | Mark Zug | |
| Best Cover Illustration - Magazine | ||
| * | Cover (Dragon Jul 2000) | Todd Lockwood |
| Cover (Dragon Jun 2000) | Brom | |
| Cover (Chicon 2000 Program (Cover A, "Sue")) | Bob Eggleton | |
| Cover (Analog Oct 2000) | Frank Kelly Freas | |
| Cover (Dreams of Decadence Summer 2000) | Jael | |
| Cover (Tomb Raider #6 Jul 2000) | Joe Jusko | |
| Cover (Heavy Metal Nov 2000) | Luis Royo | |
| Best Interior Illustration | ||
| * | Interior (Cinderella by K. Y. Craft) | Kinuko Y. Craft |
| Interior (20,000 Leagues Under the Sea by Jules Verne) | Leo Dillon and Diane Dillon | |
| Interior (MZB Fantasy Magazine Winter 2000) A Dear Gazelle | Omar Rayyan | |
| Interior (Where Have the Unicorns Gone? by Jane Yolen) | Ruth Sanderson | |
| Interior (The New Dinosaurs by William Stout) | William Stout | |
| Best Color Work - Unpublished | ||
| * | Reach | Michael Whelan |
| Dance of the Dead | H. Ed Cox | |
| Daybreak | Lubov | |
| Appointment with Death | Marianne Plumridge | |
| Berry Market | Omar Rayyan | |
| Best Monochrome Work - Unpublished | ||
| * | A Wizard of Earthsea | Drew Willis |
| The Secret Garden | Jill Bauman | |
| Anubis | Charles Keegan | |
| Enchanted Wood | Joel Keener | |
| Baby Dragon | Stanley W. Morrison | |
| Best Three-Dimensional Art | ||
| * | Millennium Angel (resin) | Sandra Lira |
| The White Dragon | Robert Belgrad | |
| Goth Faery (fimo) | Wendy Froud | |
| Bookstand (red oak, slate, glass & sterling silver) | Johnna Klukas | |
| Frazetta's Barbarian (bronze) | Clayburn Moore | |
| Best Gaming-Related Illustration | ||
| * | Crucible: Conquest of the Final Realm (FASA Game book) | Ian Miller |
| Staunch Defenders (card Art for Magic: The Gathering) | Tristan Elwell | |
| Forge of Fury (Dungeons & Dragons modules) | Todd Lockwood | |
| Star Wars RPG: Core Rule Book | Drew Struzan | |
| Best Product Illustration | ||
| * | Dracopaleontology (SFBC flyer & calendar) | Donato Giancola |
| Boucat (fine art print) | Braldt Bralds | |
| Angel (Christmas Greeting Card) | Kinuko Y. Craft | |
| Redgar (Promotional Stand-Up Display) | Todd Lockwood | |
| Everquest: The Scars of Velius (Computer Game) | Keith Parkinson | |
| Best Art Director | ||
| * | Tor Books | Irene Gallo |
| Baen Books | James P. Baen | |
| DAW Books | Sheila Gilbert | |
| Art Director TSR book line and VP of Creative Services, Wizards of the Coast | Jon Schindehette | |
| Bantam Books | Jamie Warren Youll | |
| Award for Artistic Achievement | ||
| * | ---- | Frank Kelly Freas |
| ---- | Tom Kidd | |
| ---- | Don Maitz | |
| ---- | John Jude Palencar | |
| ---- | Lisa Snellings | |
| Award for Contribution to ASFA | ||
| * | for assembling, designing & printing last year's Chesley Awards color brochure | Lockwood,Todd and Schindehette,Jon and Wizards of the Coast |
| for runing the ASFA suite at Chicon | Morgana | |
| for reorganizing and maintaining the ASFA website | Mel White | |
| Award of Distinction | ||
| * | ---- | Estate of Chesley Bonestell |