Fred and Lynn were competing for a perfect-score bonus; otherwise, their subject would not have been played. Dick didn't exactly let Jan down easy with that "destined to lose" remark!
The only time I ever saw Didi Conn play the Winners Circle was during that infamous 'Famous Losers' episode when she gave an unspecific clue that had cost a contestant (I think his name was Jackie, but uncertain) $20,000. What was unusual, though, was the judges' buzzer sounded off 30+ seconds after they celebrated a win that almost was.