This is something I have been suggesting on PC Graal since maybe 2004 or 2005ish. I started working on the foundations of it on Babylon and ended up leaving the game for a while before it really materialized.
I don't know if iClassic has a big enough pool of events for automation to work properly. Only certain events can be automated. Ice race, bush race, and horse races could all be automated. For them to be automated would require that iClassic have very polished hack detection of all sorts, though.