How much money has Microsoft paid out until now? That's a tough question. Microsoft has been paying out large amounts of money to states, individuals and companies alike.
A July 2005 figure shot to $9 billion while others put it at nearly $7 billion. Anyway, that figure is bound to increase in the forthcoming months if Microsoft does not comply with the European Commission's requests.
The Seattle based company might become the first company ever to pay more than $10 billion in lawsuits and settlements. But Microsoft isn't any company. It has more than $33 billion in cash and is expected to earn more than $50 billion in 2007 when the world welcomes new versions of Windows Vista and Microsoft Office 2007.
There's a long list of Microsoft (and Apple) related lawsuits and patent disputes maintained by an enthusiast here.