In the 60's my friend and his brother in law, who was always up to some shennanigans, drive out to Santa Anita at 3 in the morning. The brother in law takes a huge needle out of the trunk and goes into the stables and shoots up some horse with something. The next day my friend, his brother in law, and their buddies beg, borrow and steal everyting they can get and put it down on this horse. The race goes off - horse is higher than a kite and comes in dead last.
Also - I think it is in the book "Goodfellas" [not the movie]. Henry Hill and his buddies lost a ton of money on a fixed basketball game.