CODiE Awards: 1986
The SIIA CODiE Awards are one of the oldest still around. The first games were awarded in 1986. Cold war was a reality, USSR was a superpower and most of you weren't even born.
Here's a description from the official site: "The SIIA CODiE Awards were established in 1986 so that pioneers of the then-nascent software industry could evaluate and honor each other's work. During the years that followed, the program evolved into three tracks (content, education, and software) and then further evolved into two (business technology and education technology) — but our core mission has always remained the same: recognizing excellence by honoring the software and information industry's leading products and services."