Historical clue formulations

• Lose one's shirt, say — 2023-05-03
• Experience financial ruin — 2022-05-08
• Flop — 2020-10-10
• Lose an all-in hand, say — 2018-08-12
• Totally fail — 2011-04-17
• Lose one's shirt, in business — 2011-02-15
• Lose one's shirt — 2010-11-12
• Lose one's shirt — 1999-03-05
• Lose everything — 1999-02-28