- Award Category: Best Gaming-Related Illustration Award Category Record # 153
- Award Type: Chesley Award
- Display Order: 500
| 1999 | ||
|---|---|---|
| Win | Dragonlance Classics 15th Anniversary Game Module | Todd Lockwood |
| Nomination | Alternity: Player's Handbook & Game Guide | R. K. Post |
| Nomination | Ertai, Wizard Adept | Terese Nielsen |
| Nomination | Plainscape: The Inner Plains | Brom |
| 2000 | ||
| Win | Duelist | Brom |
| Nomination | Creatures of the Night | Todd Lockwood |
| Nomination | Dune | Carol Heyer |
| Nomination | Ivy Scholar | Donato Giancola |
| Nomination | Unmask | R. K. Post |
| 2001 | ||
| Win | Crucible: Conquest of the Final Realm | Ian Miller |
| Nomination | Forge of Fury | Todd Lockwood |
| Nomination | Star Wars RPG: Core Rule Book | Drew Struzan |
| Nomination | Staunch Defenders | Tristan Elwell |
| 2002 | ||
| Win | Shivan Dragon | Donato Giancola |
| Nomination | Hackmaster: The Player's Book | Ruth Thompson |
| Nomination | Lightning Angel | R. K. Post |
| Nomination | Lord of the Iron Fortress | Todd Lockwood |
| Nomination | Respite | William O'Connor |
| 2003 | ||
| Win | Spider Queen | Todd Lockwood |
| Nomination | Darkness and Light | William Hammock |
| Nomination | Mirari's Wake | David Martin |
| 2004 | ||
| Win | Draconomicon | Todd Lockwood |
| Nomination | Cavern of the Snow Witch | Les Edwards |
| Nomination | Silver Dragons | Richard Sardinha |
| Nomination | Sword of Caldra | Donato Giancola |
| Nomination | Unapproachable East | Matt Wilson |
| 2005 | ||
| Win | Monte Cook's Arcana Unearthed | Mark Zug |
| Nomination | Boneclaw | Dave Allsop |
| Nomination | Creature of Havoc | Les Edwards |
| Nomination | Sea Kin Haggling | Ed Cox |
| Nomination | Training a Dire Badge | William O'Connor |
| 2006 | ||
| Win | Blazing Archon |
Gabor Szikszai?Gabor Szikszai
and
Zoltan Boros?Zoltan Boros
|
| Nomination | A Family Affair | Richard Sardinha |
| Nomination | Keeper of Water | William O'Connor |
| Nomination | Lords of Madness: The Book of Aberrations | Wayne England |
| Nomination | Standing Wave | Franz Vohwinkel |
| 2007 | ||
| Win | Dragons of Faerun | Todd Lockwood |
| Nomination | An Ill Wind Blows | Carl Critchlow |
| Nomination | Coils of Set | Richard Sardinha |
| Nomination | Knightly Order of Ansalom | Paul Bielaczyc and Michael Bielaczyk |
| Nomination | Seed of Undead | Eva Widerman |
| Nomination | Thri-Keen | Ralph Horsley |
| 2008 | ||
| Win | Vanguard: Saga of Heroes | Donato Giancola |
| Nomination | Du'ulora Quori | James Zhang |
| Nomination | Holy Strength | Terese Nielsen |
| Nomination | Kalaak Raider | Lucio Parrillo |
| Nomination | Lady Tureya | Ron Lemen |
| Nomination | Nebin & the Gargoyles | Carl Frank |
| Nomination | Nova Chaser | Dan Scott |
| Nomination | Oros the Avenger | Daren Bader |
| Nomination | Riftmarked Knight | William O'Connor |
| Nomination | Scion: Hero | Michael Komarck |
| Nomination | The Sinister Spire | Wayne England |
| 2009 | ||
| Win | Stoic Angel | Volkan Baga |
| Nomination | Angelic Benediction | Michael Komarck |
| Nomination | Cancel | David Palumbo |
| Nomination | Firestorm | Tom Fleming |
| Nomination | Invincible Hymn | Matt Stewart |
| 2010 | ||
| Win | Silverwing | Lucas Graciano |
| Nomination | Boarguts the Impaler | Daren Bader |
| Nomination | Joraga Bard | Volkan Baga |
| Nomination | Kalitas, Bloodchief of Ghet | Todd Lockwood |
| Nomination | Lorthos the Tidemaker | Kekai Kotaki |
| Nomination | Serendib Efreet | Matthew Stewart |
| 2011 | ||
| Win | Amorphous Drake | Lucas Graciano |
| Nomination | Bloodshot Trainee | Matthew Stewart |
| Nomination | Eel Umbra | Howard Lyon |
| Nomination | Gaea's Revenge | Kekai Kotaki |
| Nomination | Harbor Serpent | Daarken |
| Nomination | Maritime Guard | L. A. Williams |
| 2012 | ||
| Win | Distress | Michael C. Hayes |
| Nomination | Creepy Doll | Matt Stewart |
| Nomination | Glissa, the Traitor | Chris Rahn |
| Nomination | Pathfinder Player Companion: The Humans of Golarian | Lucas Graciano |
| Nomination | Wandering Elf | E. M. Gist |
| 2013 | ||
| Win | Ereshkigal, Death Mistress | David Palumbo |
| Nomination | Chandra the Firebrand | D. Alexander Gregory |
| Nomination | Dragon Swarm | Lucas Graciano |
| Nomination | Princess of the Underworld | James Ryman |
| Nomination | Thundermaw Hellkite | Sverlin Velinov |
| 2014 | ||
| Win | The Last Stand of Thorin Oakenshield | Lucas Graciano |
| Nomination | Ashen Rider | Chris Rahn |
| Nomination | Observant Alseid | Todd Lockwood |
| Nomination | Prognostic Sphinx | Steve Prescott |
| Nomination | Ruric: Thar the Unbowed | Tyler Jacobson |
| Nomination | Serene Rememberance | David Palumbo |
| 2015 | ||
| Win | Pharika, God of Affliction | Peter Mohrbacher |
| Nomination | Ajani the Steadfast Magic card | Chris Rahn |
| Nomination | D&D The Rise of Tiamat | Michael Komarck |
| Nomination | Drown in Sorrow Magic card | Noah Bradley |
| Nomination | Ephara, God of Polis Magic card | Eric Deschamps |
| Nomination | Ghoulcaller Gisa Magic card | Karla Ortiz |
| 2016 | ||
| Win | Fruit of the First Tree - Fate Reforged Magic Card | Ryan Yee |
| 2017 | ||
| Win | Die Young, Kaladesh card set | Ryan Yee |
| Nomination | Encounter at Stygeon Prime- Star Wars: The Card Game | Mauricio Calle |
| Nomination | Inventor's Apprentice Kaladesh card set | Ryan Pancoast |
| Nomination | Long-Finned Skywhale Kaladesh card set | Cliff Childs |
| Nomination | Mastertrinketeer Kaladesh card set | Matthew Stewart |
| 2018 | ||
| Win | Offering Sagaborn RPG Core Rule Book | Melissa Gay |
| Nomination | Chandra Gremlin Wrangler Heroes of the Realm | Kari Christensen |
| Nomination | Compulsive Research Magic card for Modern Masters 2017 | Sara Winters |
| Nomination | Moaning Wall Magic card for Hour of Devastation | Piotr Jabloński |
| Nomination | The Ur- Dragon Magic card for Commander 2017 | Jaime Jones |
| 2019 | ||
| Win | Frantic Search | Mitchell Malloy |
| Nomination | Bitterblossum | Jesper Ejsing |
| Nomination | Feasting Hunger | Kari Christensen |
| Nomination | Glowspore | Lars Grant-West |
| Nomination | Knight of Autumn | Ryan Pancoast |
| Nomination | Octopus Umbra | Howard Lyon |
| 2020 | ||
| Win | King By His Own Hand | Charles Urbach |
| Nomination | Brazen Borrower: Throne of Eldraine Magic Card | Iris Compiet |
| Nomination | Flaxen Intruder: Throne of Eldraine Magic Card | Omar Rayyan |
| Nomination | Lonesome Unicorn: Throne of Eldraine Magic Card | Winona Nelson |
| Nomination | Rosethorn Acolyte: Throne of Eldraine Magic Card | Wylie Beckert |
| Nomination | Summer Dandelion: Olde Fae Card Game | Melissa Gay |
| 2021 | ||
| Win | Sublime Epiphany | Lindsey Look |
| Nomination | Cuombajj Witches | Seb McKinnon |
| Nomination | Dissident Whispers cover | Jabari Weathers |
| Nomination | Overlight: The Lost Spire of Tziuhquatl | Joanna Barnum |
| Nomination | Roswell Skateboard | Christian Piccolo |
| Nomination | The Whispering Heart | Charles Urbach |