You are confusing a Win Loss Statement sent by casinos and the cruiseline casino departments with a 1099. They are not the same thing. Casino winnings aren't reported on a 1099. Occasionally 1099s are sent for certain casino gift drawings. For example, on Carnival cruises, on an Ultra cruise where there's a drawing and guarantee winning of a gift or Freeplay, Carnival issues a 1099 for the value of the gift or Freeplay that everyone that signed up for the Ultra cruise will receives.