The oldest extant site I had anything to do with appears to be https://park.org/ https://park.org/. My bit was the IBM Chess Challenge that seems to have evapor

The oldest extant site I had anything to do with appears to be https://park.org/ https://park.org/. My bit was the IBM Chess Challenge that seems to have evaporated. But you can see one problem with keeping a site up for 26 years. park.org is heavily imagemap dependent. Imagemaps used to be processed server side, and eventually flipped to be browser side, but required the map to be sent to the browser. No one has updated the park.org HTML to reflect this so the imagemap based navigation doesn't work. And someone does appear to be doing some sort of maintenance because the links to the 1996 Chess Challenge site appear to have been removed whenever IBM lost interest in keeping that site up.