Here are some copyright infringement cases which have resulted in substantial losses to the infringer:
Davidson v. United States No. 13-942C - US Copyright Office - A picture of a replica of the Statue of Liberty in Las Vegas was reprinted on a U.S. postage stamp under the mistaken belief that the photograph was of the original statue in New York. The artist who created that statue located in Las Vegas, Mr. Davidson, was awarded $3.5 million dollars plus interest.
Rogers v. Koons, 960 F.2d 301 (2d Cir. 1992) - US Copyright Office - Jeff Koons, an artist, used Art Roger's photograph of a couple holding a line of puppies to create a sculpture. The artist lost and paid the photographer a confidential settlement.
Walt Disney Prods. v. Air Pirates, 581 F.2d 751 (9th Cir. 1978) - A group of cartoonists calling themselves the Air Pirates reused Walt Disney characters in their underground comic. Disney was awarded $190,000 in damages and $2,000,000 in legal fees, but settled for less 9 years later.