| Year | Category | Winners and nominees | Developer/Publisher |
| 1997 | CD-ROM
Educational – Children | 101 Dalmatians Storybook | Disney Interactive |
| 1997 | CD-ROM
Educational – Children | Freddi Fish 2: The Case of the Haunted Schoolhouse | Humongous Entertainment |
| 1997 | CD-ROM
Educational – Children | Living Books: Sheila Rae, The Brave | Wanderful interactive storybooks |
| 1997 | CD-ROM
Educational – Children | The Simpsons: Cartoon Studio | Big Top Productions / Fox Interactive |
| 1997 | CD-ROM
Educational – Children | Snoopy's Campfire Stories | Virgin Sound & Vision |
| 1997 | CD-ROM
Entertainment | Cinemania 97 | Microsoft |
| 1997 | CD-ROM
Entertainment | Encarta 97 – Encyclopedia Deluxe | Microsoft |
| 1997 | CD-ROM
Entertainment | Eyewitness Encyclopedia of Space and the Universe | DK |
| 1997 | CD-ROM
Entertainment | Inside Independence Day | Fox Interactive |
| 1997 | CD-ROM
Entertainment | Leonardo da Vinci | Coris Publishing |
| 1997 | CD-ROM
Game | Monty Python & the Quest for the Holy Grail | 7th Level / Panasonic |
| 1997 | CD-ROM
Game | Descent II | Parallax Software / Interplay Productions |
| 1997 | CD-ROM
Game | Goosebumps | DreamWorks Interactive |
| 1997 | CD-ROM
Game | Quake | id Software / GT Interactive |
| 1997 | CD-ROM
Game | Warcraft II: Beyond the Dark Portal | Cyberlore Studios / Blizzard Entertainment |
| 1998 | CD-ROM
Entertainment | Blade Runner | Westwood Studios / Virgin Interactive |
| 1998 | CD-ROM
Entertainment | Hercules | Eurocom / Disney Interactive Software |
| 1999 | CD-ROM
Entertainment | Big Brother | Media X |
| 1999 | CD-ROM
Entertainment | Baldur's Gate | BioWare / Black Isle Studios, Interplay Entertainment |
| 1999 | CD-ROM
Entertainment | Heretic II | Raven Software, Loki Software, Hyperion Entertainment / Activision |
| 1999 | CD-ROM
Entertainment | Rainbow Six | Ubisoft, Red Storm Entertainment / Ubisoft |
| 1999 | CD-ROM
Entertainment | Unreal | Epic MegaGames, Digital Extremes, Legend Entertainment / GT Interactive |
| 2000 | CD-ROM
Game | NBA Pro Basketball | Konami |
| 2000 | CD-ROM
Game | Duke Nukem: Time to Kill, Duke Nukem: Total Meltdown, and Duke Nukem 3D
For the Duke Nukem series. | 3D Realms / GT Interactive |
| 2000 | CD-ROM
Game | MechWarrior 3 | Zipper Interactive / MicroProse |
| 2000 | CD-ROM
Game | Star Wars Jedi Knight: Dark Forces II | LucasArts / LucasArts |
| 2000 | CD-ROM
Game | Doom II: Hell on Earth | id Software / GT Interactive |
| 2000 | CD-ROM
Industry | Interact Media Solution | |
| 2000 | CD-ROM
Industry | Final Draft 5.0 | Final Draft |
| 2000 | CD-ROM
Industry | Quicken 2000 | Quicken |
| 2000 | CD-ROM
Industry | Final Cut Pro | Apple |
| 2001 | Computer
Educational | Family Tree Maker 8.0 Deluxe | Ancestry.com |
| 2001 | Computer
Educational | Acid DJ 2.0 | Sony Creative Software |
| 2001 | Computer
Educational | Barbie Magic Genie Bottle | Vicarious Visions / Mattel Interactive |
| 2001 | Computer
Educational | Nancy Drew: Message in a Haunted Mansion | Her Interactive / DreamCatcher |
| 2001 | Computer
Software | Adobe Photoshop 6.0 | Adobe Systems |
| 2001 | Computer
Software | Giants: Citizen Kabuto | Planet Moon Studios / Interplay Entertainment |
| 2001 | Computer
Software | Mechanical Warrior IV | FASA Interactive / Microsoft |
| 2001 | Computer
Software | The Sims | Maxis / Electronic Arts |
| 2001 | Computer
Software | Tomb Raider: Chronicles | Core Design / Eidos Interactive |
| 2001 | Video Game | Perfect Dark | Rare / Rare, Nintendo |
| 2001 | Video Game | FIFA 2001 Major League Soccer | EA Sports / Electronic Arts |
| 2001 | Video Game | Final Fantasy IX | Square / Square Enix |
| 2001 | Video Game | 007: The World Is Not Enough | Eurocom / Electronic Arts |
| 2001 | Video Game | Quake II | id Software / Activision |
| 2002 | Video Game | Final Fantasy VIII | Square |
| 2002 | Video Game | Command & Conquer: Red Alert 2 | Westwood Pacific / Electronic Arts |
| 2002 | Video Game | Myst, Riven: The Sequel to Myst, and Myst III: Exile
For the Myst series. | Cyan Worlds, Presto Studios / Broderbund, Red Orb Entertainment, Ubisoft |
| 2002 | Video Game | Tony Hawk's Pro Skater 2 | Neversoft / Activision |
| 2002 | Video Game | Quake III: Arena | id Software / Activision |
| 2002 | Computer
Software | Final Cut Pro 2.0 | Apple |
| 2002 | Computer
Software | Avid Xpress DV | Avid |
| 2002 | Computer
Software | Premiere 6.0 | Adobe Systems |
| 2002 | Computer
Software | Macromedia Flash 5.0 | Macromedia |
| 2002 | Computer
Software | Final Draft 5.0 | Final Draft |