The following are the winners of the 26th annual (1999) Origins Award, presented at Origins 2000:
| Category | Winner | Company | Designer(s) |
|---|---|---|---|
| Best Abstract Board Game of 1999 | Button Men | Cheapass Games | Designer: James Ernest |
| Best Action Computer Game of 1999 | MechWarrior 3 | Microprose, Inc. | Designers: Graham Kays, Michael Mancuso, Erol Oms, Rob Sears, George Sinfield, Brian Soderberg |
| Best Amateur Game Magazine of 1999 | Alarums & Excursions | Lee Gold | Publisher: Lee Gold |
| Best Card Game Expansion or Supplement of 1999 | 7th Sea: Strange Vistas | Alderac Entertainment Group | Designers: Dan Verssen, Rob Vaux, Kevin Wilson |
| Best Game-Related Novel of 1999 | Delta Green: The Rules of Engagement | Pagan Publishing | Author: John Tynes |
| Best Game-Related Short Work of 1999 | Just a Tad Beyond Innsmouth | Chaosium, Inc. | Author: Stanley C. Sargent |
| Best Graphic Presentation of a Board Game of 1999 | Button Men | Cheapass Games | Designer: James Ernest |
| Best Graphic Presentation of a Card Game or Supplement of 1999 | 7th Sea: No Quarter! | Alderac Entertainment Group | Designers: Dan Verssen, David Williams, John Zinser |
| Best Graphic Presentation of a Roleplaying Game, Adventure, or Supplement of 1999 | Dark*Matter | Wizards of the Coast | Designers: Wolfgang Bauer, Monte Cook |
| Best Historical Board Game of 1999 | Great War at Sea: 1904–1905, The Russo-Japanese Naval War | Avalanche Press | |
| Best Historical Figure Miniature Series of 1999 | German Assault Squad | Easy Eight Enterprises | |
| Best Historical Miniatures Rules of 1999 | Armies of Antiquity | Warhammer Historical Wargames | |
| Best Ongoing Play-by-Mail Game of 1999 | Middle-earth PBM Fourth Age, circa 1000 | Game Systems, Inc. | Designers: William B. Feild, Jr., Peter G. Stassun |
| Best Professional Game Magazine of 1999 | Knights of the Dinner Table Magazine | Kenzer & Company | Developers: Jolly Blackburn, Brian Jelke, Steve Johansson, David Kenzer |
| Best Roleplaying Adventure of 1999 | Beyond the Mountains of Madness | Chaosium, Inc. | Designers: Charles Engan and Janyce Engan |
| Best Roleplaying Computer Game of 1999 | Baldur's Gate: Tales of the Sword Coast | Interplay Productions | |
| Best Roleplaying Game of 1999 | 7th Sea Role-Playing Game | Alderac Entertainment Group | Designers: John Wick, Jennifer Wick, Kevin Wilson |
| Best Roleplaying Supplement of 1999 | Delta Green: Countdown | Pagan Publishing | Designers: Dennis Detwiller, Adam Scott Glancy, John Tynes |
| Best Science Fiction or Fantasy Board Game of 1999 | Orcs at the Gates | Jolly Roger Games | Designer: Jim Dietz |
| Best Science Fiction or Fantasy Figure Miniature of 1999 | Togashi Yokuni | Alderac Entertainment Group | Designer: Chaz Elliot |
| Best Science Fiction or Fantasy Miniatures Rules of 1999 | Diskwars | Fantasy Flight Games | Designers: Tom Jolly, Christian T. Petersen |
| Best Strategy Computer Game of 1999 | Sid Meier's Alpha Centauri | Firaxis | Designers: Sid Meier, Brian Reynolds |
| Best Trading Card Game of 1999 | 7th Sea: No Quarter! | Alderac Entertainment Group | Designers: Dan Verssen, David Williams, John Zinser |
| Best Traditional Card Game of 1999 | Chez Geek | Steve Jackson Games | Designer: Jon Darbro |
| Best Vehicle Miniature of 1999 | Babylon 5 Station | Agents of Gaming | Sculptor: John Winters |
| Adventure Gaming Hall of Fame | Champions | Hero Games | |
| Adventure Gaming Hall of Fame | GURPS | Steve Jackson Games | |
| Adventure Gaming Hall of Fame | Greg Costikyan | ||
| Adventure Gaming Hall of Fame | Larry Elmore |