With regular jockey René Douglas in the saddle, she seemed to tire in the stretch in the Kentucky Oaks and placed 6th to Rags to Riches.
Returned to the turf, she won the Double Delta Stakes at Arlington Park and the Virginia Oaks at Colonial Downs gate to wire.
On October 13, 2007, Dreaming of Anna was beaten by a little over 2 lengths by Bit of Whimsy in the Grade I Queen Elizabeth II Challenge Cup Stakes at Keeneland Race Course after leading most of the way.
Dreaming of Anna made her 2008 racing debut at Tampa Bay Downs with a win in the Endeavour Breeders' Cup Stakes.
Dreaming of Anna was retired from racing in October 2008 and was shipped to Three Chimneys Farm, where she was to be bred to Street Cry.