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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 (The Howling Stones by Alan Dean Foster) | Bob Eggleton |
| Cover (Things Left Behind by Gary Braunbeck) | Alan M. Clark | |
| Cover (Corum: The Coming of Chaos by Michael Moorcock) | Don Maitz | |
| Cover (Lady of Avalon by Marion Zimmer Bradley) | John Jude Palencar | |
| Cover (The Mageborn Traitor by Melanie Rawn) | Michael Whelan | |
| Best Cover Illustration - Paperback | ||
| * | Cover (The Rhinocerous Who Quoted Nietzche and Other Odd Acquaintancs by Peter S. Beagle) | Michael Dashow |
| Cover (Competitions by Sharon Green) | Thomas Canty | |
| Cover (The Stone Prince by Fiona Patton) | Jody Lee | |
| Cover (The Wayward Knights by Roland Green) | Todd Lockwood | |
| Cover (Merlin's Harp by Anne Eliot Crompton) | Don Maitz | |
| Cover (Jovah's Angel by Sharon Shinn) | John Jude Palencar | |
| Cover (A Game of Thrones by George R. R. Martin) | Stephen Youll | |
| Best Cover Illustration - Magazine | ||
| * | Cover (Dragon Aug 1997) | Todd Lockwood |
| Cover (Heavy Metal May 1997) | Olivia de Berardinis | |
| Cover (Analog Oct 1997) [O Pioneer! by Frederik Pohl] | Bob Eggleton | |
| Cover (Realms of Fantasy Apr 1997) | Don Maitz | |
| Cover (F&SF Apr 1997) | Barclay Shaw | |
| Best Interior Illustration | ||
| * | Interior (The Hobbit by J. R. R. Tolkien) | Alan Lee |
| Interior ("Repent, Harlequin!", Said the Ticktockman by Harlan Ellison) | Rick Berry | |
| Interior (Fractures in Rhyme - Art Against AIDS Project) The Queen of Hearts | Thomas Canty | |
| Interior (A Diversity of Dragons by Anne McCaffrey & Richard Woods) | John Howe | |
| Interior (MZB Fantasy Magazine, Autumn 1997) [Grey by Mercedes Lackey] | Nicholas Jainschigg | |
| Interior (SF Age Nov 1997) [On the Inside by Robert Silverberg] | Todd Lockwood | |
| Best Unpublished Illustration - Color | ||
| * | Painting (Private Commission) The Astronomer Prince | Stephen Hickman |
| Display (DragonCon 1997) Michael the Archangel | Greg Hildebrandt and Tim Hildebrandt | |
| Display (LoneStarCon II) Chasing the Wind | Don Maitz | |
| Display (LoneStarCon II) Perrin, Queen of Autumn | Jennifer Emmett Weyland | |
| Best Unpublished Illustration - Monochrome | ||
| * | Painting () Silently Moving People | Joy Marie Ledat |
| Display (DragonCon 1997) Teenage Angst | Charles Keegan | |
| Display (DragonCon 1997) Mr. Buttons | Richard Kirk | |
| Display (LoneStarCon II) Harlequin | Erin McKee | |
| Display (Oasis 11) the Hatchling | Stanley W. Morrison | |
| Display (DragonCon 1997) Callisto | Jeff Pitarelli | |
| Best Three-Dimensional Art | ||
| * | Witchblade (coldcast porcelain) | Clayburn Moore |
| Gandalf the Gray (mixed media) | Daniel Horne | |
| Reach (bronze) | J. A. Pippett | |
| Princess Holly (mixed media) | Laura Reynolds | |
| Dragonheart (coldcast porcelain) | The Schifflet Brothers | |
| Best Art Director | ||
| * | Bantam Books | Jamie Warren Youll |
| DNA Publications | Warren Lapine | |
| Warner Books | Don Puckey | |
| Random House/Ballantine Books | David Stevenson | |
| Wizards of the Coast | Matt Wilson | |
| Award for Artistic Achievement | ||
| * | ---- | Vincent Di Fate |
| ---- | Rick Berry | |
| ---- | Olivia de Berardinis | |
| ---- | Alan Lee | |
| ---- | Syd Mead | |
| ---- | John Jude Palencar | |
| ---- | Bernie Wrightson | |
| Award for Contribution to ASFA | ||
| * | for work above and beyond the call of duty as ASFA President | Janny Wurts |
| ---- | Jane Frank | |
| ---- | Todd Lockwood | |
| ---- | Morgana | |
| ---- | Teresa Patterson | |