The competition's very first run in 1995 split the entries into two categories: one for games written with Inform, and one for TADS. Therefore, that year had two first-place winners, two second-place winners, and so on...
| 1st place (tie) | A Change in the Weather by Andrew Plotkin |
| 1st place (tie) | Uncle Zebulon's Will by Magnus Olsson |
| 2nd place (tie) | The Mind Electric by Jason Dyer |
| 2nd place (tie) | Toonesia by Jacob Weinstein |
| 3rd place (tie) | The Magic Toyshop by Gareth Rees |
| 3rd place (tie) | The One That Got Away by Leon Lin |
| 4th place (tie) | Mystery Science Theater 3000 Presents "Detective" by C. E. Forman, Graeme Cree, and Stuart Moore |
| 4th place (tie) | A Night at the Museum Forever by Chris Angelini |
| 4th place (tie) | Undertow by Stephen Granade |
| 5th place | All Quiet on the Library Front by Michael S. Phillips |
| 6th place (tie) | Tube Trouble by Richard Tucker |
| 6th place (tie) | Undo by Neil deMause |
The organizer of the 1995 Annual Interactive Fiction Competition was Kevin Wilson.