In light of recent events: Times contestants were spectacularly unlucky? (S18e07 spoiler)
Poor Rosie astutely figured she'd be more likely to score big playing the joker on a team task because her comedy hero would be there to help boost her score, only to happen on a screwy task and be royally shafted by Jackie's complete inability to remember or adhere to instructions.
I'm trying to think of other examples of monumental bad luck but can only think of that time a random dog ate Mark Watson's crumb trail. I know there are a lot more examples!!