Money losing would be much more of a shock than Tyson losing to Douglas IMO

Seriously man, reality check please!

Douglas upsetting Tyson wasn't just the biggest upset in boxing history, many see it as one of the biggest upsets in sports history... usually at least top5 :deal

examples:
#3
http://bleacherreport.com/articles/1036181-the-50-biggest-upsets-in-sports-history/page/49
#4
http://www.toptenz.net/top-10-upsets-in-sports-history.php