Gambler's Woe is a term used to describe the financial and emotional distress experienced by someone who has been gambling and has accumulated DEBT or experienced a streak of bad luck. The two crossword solutions for Gambler's Woe are DEBT (4 letters) and STREAKOFBADLUCK (15 letters). DEBT is a common consequence of gambling, as it can be difficult to keep track of how much money has been spent. A streak of bad luck is also a common occurrence in gambling, as luck is an unpredictable factor. Both of these can lead to Gambler's Woe, which can have serious consequences for the gambler.