| 1st place | Winter Wonderland by Laura Knauth |
| 2nd place | For a Change by Dan Schmidt |
| 3rd place | Six Stories by Neil K. Guy |
| 4th place | A Day for Soft Food by Tod Levi |
| 5th place | Exhibition by Ian Finley |
| 6th place | Halothane by Ravi Rajkumar |
| 7th place | On the Farm by Lenny Pitts |
| 8th place | Hunter, in Darkness by Andrew Plotkin |
| 9th place | Beat the Devil by Robert M. Camisa |
| 10th place | Jacks or Better to Murder, Aces to Win by J. D. Berry |
| 11th place | Erehwon by Richard Litherland |
| 12th place | Lunatix - The Insanity Circle by Mike Snyder |
| 13th place | Bliss by Cameron Wilkin |
| 14th place | Stone Cell by Steve Kodat |
| 15th place | Four Seconds by Jason Reigstad |
| 16th place | The HeBGB Horror! by Eric Mayer |
| 17th place | Only After Dark by Gunther Schmidl |
| 18th place | A Moment of Hope by Simmon Keith |
| 19th place | Chaos by Shay Caron |
| 20th place | Strangers in the Night by Rich Pizor |
| 21st place | Lomalow by Brendan Barnwell |
| 22nd place | King Arthur's Night Out by Mikko Vuorinen |
| 23rd place | Calliope by Jason McIntosh |
| 24th place | Music Education by Bill Linney |
| 25th place | Spodgeville Murphy and the Jewelled Eye of Wossname by David Fillmore |
| 26th place | Life on Beal Street by Ian Finley |
| 27th place | Remembrance by Casey Tait |
| 28th place | Thorfinn's Realm by Robert Hall and Roy Main |
| 29th place (tie) | Death to my Enemies by Jon Blask (as Roody Yogurt) |
| 29th place (tie) | The Water Bird by Athan Skelley |
| 31st place | Chicks Dig Jerks by Robb Sherwin |
| 32nd place | SNOSAE by R. Dale McDaniel |
| 33rd place | Pass the Banana by Admiral Jota |
| 34th place | Outsided by Chad Elliott |
| 35th place | Lurk. Unite. Die. Invent. Think. Expire. by Ryan Stevens |
| 36th place | Guard Duty by Jason F. Finx |
| 37th place | Skyranch by Jack Driscoll |
The organizer of the 1999 Annual Interactive Fiction Competition was Stephen Granade.