The term 'Losing Casino Roll' refers to a situation in which a gambler has lost all of their money at a casino. The two crossword solutions for this term are 'CRAP' (4 letters) and 'SNAKEEYES' (9 letters). 'CRAP' is a slang term for dice, which are commonly used in gambling games. 'SNAKEEYES' is a term used to describe the result of rolling two ones on a pair of dice, which is the worst possible outcome for a gambler.