The oldest WSGF Certified game is Total Annihilation, which was released in 1997. It's essentially a 2D game, and while the game is better in widescreen, it's unlikely that it was specifically intended to be that way. The screen change is based on resolution, not aspect ratio.
The oldest *3D* WSGF Certified game is Enclave, released in 2002. Its screen change is based on aspect ratio. The wider your monitor, the more you see.
The oldest game that supports multiple aspect ratios both correctly and intentionally is Command & Conquer, released in 1995. It has a 4:3 mode and a 16:10 mode. It's anamorphic 16:10, which means the 4:3 mode has black bars and the 16:10 mode doesn't.
The oldest 3D game that supports multiple aspect ratios is Dark Forces II: Jedi Knight, released in 1997. Also released in 1997 is Dungeon Keeper, but JK2's support is better because it supports more resolutions. Both of these games are vert -.
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