The Legends League may well be the oldest active simracing league in the world. Its origins lie in the SPRTSMS forum of Compuserve, when a group of racing enthusiasts founded F1SA (Formula 1 Simulators Association) - to keep their messages apart from the golf simmers!
That was in 1993, when HTML, email and the world wide web were largely unknown. We raced F1GP (known as World Circuit in the USA and Canada) and GP2 by Microprose, and Indycar Racing 2 by Papyrus. Mostly with keyboard or joystick, wheels and pedals being rare in those days. Consequently very few people managed to race without driving aids, those that did were called Water Walkers. And oh yes, the racing was done offline exclusively. Multiplayer didn’t exist. It was basically a hot lapping competition, as well as full length off-line racing against the AI and then comparing authenticated race times to decide the league's human (and alien even then!) winners.
All that changed on October 9, 1998, when simracing took a giant leap: Papyrus introduced Grand Prix Legends. This sim featured a sophisticated physics model and, even more important, multiplayer racing over the internet. In 1999, one of its beta-testers and distinguished member of F1SA, Joachim Trensz, ported the whole community to e-Groups (now Yahoo groups) and re-baptized it to Legends League. We no longer use GPL, but the name will remain. It doesn’t reflect the quality of our driving but our origins.
Grand Prix Legends was succeeded, after a few years of low league activity, by the Trans-Am mod for Papyrus’ Nascar Racing 2003. The physics and the racing were good, but the tin-topped cars didn’t spark much enthusiasm. After a brief spell of frantic racing the league turned dormant once again.
In September 2005, ISI [Image Space Inc.] sent a wake-up call: rFactor turned out to be another step up in realism. When the F3 Euroseries mod was added, we were wide awake. These were easily the best simulated open wheelers we had ever driven! The Legends Trans World Formula 3 championship (or TWF3) was organized. When the GP79 mod for rFactor came out, the Trans World Formula 1 championship (or TWF1) was added. Since then numerous rfactor championships have been organized with different mods along side the main GP79 series. Off season, Special and Annual events are on the calendar every season as well.
In 2012, ISI released it's follow up sim to the very successful rFactor, rFactor2. With a more sophisticated graphics and physics engine it takes the basic format and style of rFactor and pushes the limits once again. Beginning in 2014, Legends will start it's first full time rFactor2 series after months of testing.
Dropping XP I get, Microsoft officially dropped support some time ago. But Server 2003 is still in support scope until Summer 2015. This announcement is a bit on the short notice side of things, especially for something like a server OS change. We've been struggling to keep members interested in rF2 through all the builds as it was, losing our server might just be the kill shot. 
