We all know that feeling of regret after making a silly bet and losing badly. Whether it’s $5 or $500, no one likes to lose money on a bet. To help you avoid making the same mistakes, we’ve compiled a list of the worst lost bets in history. From outrageous wagers gone wrong to costly gambles that simply didn’t pay off, these stories are sure to make you think twice before placing your next bet.

1) The Sydney Harbour Bridge Bet: In 1932, two Australian friends made a bet over who could walk across Sydney Harbour Bridge first. One man won the bet, but at what cost? He was arrested and fined for trespassing!

2) The Cabbage Patch Kids Bet: In 1983, two friends in New York made a bet over who could collect the most Cabbage Patch Kids dolls. The loser had to buy the winner a new car. After months of collecting, the loser ended up with over 1,000 dolls and had to pay out over $10,000!

3) The Tiger Woods Bet: In 1998, two friends in California made a bet over who could get a picture with Tiger Woods. The loser had to buy the winner a new car. After years of trying, the loser finally met Tiger Woods… but was only able to get an autograph. He still had to pay out for the new car!

4) The Boat Race Bet: In 2004, two British friends made a bet over who could row the fastest from London to Oxford. The loser had to buy the winner a new car. After days of rowing, the loser finally arrived in Oxford… but was so exhausted that he had to be taken to the hospital!

5) The Hollywood Sign Bet: In 2006, two American friends made a bet over who could climb to the top of the Hollywood sign the fastest. The loser had to buy the winner a new car. After hours of climbing, the loser finally reached the top… but was then arrested by police!

These are just some of the worst lost bets in history. So next time you’re thinking about making a bet, remember these stories and think twice! You don’t want to end up like these poor souls.

Worst lost bets of all time

1. The world’s longest recorded losing streak in gambling history goes to Ashley Revell, who lost an astounding $127 million over the course of seven years.

2. Not to be outdone, British gambler Terry Watanabe lost a whopping $100 million in just one year, 2007.

3. Gambler Kerry Packer is said to have lost $20 million in a single night while playing baccarat in Las Vegas.

4. Another high roller, Australian businessman Matthew Reed, lost $17.5 million playing craps in just two hours while on vacation in Atlantic City.

5. Hong Kong poker player Stanley Ho is rumored to have blown through $16 million in a single sitting.

6. American businessman and high roller Terrence Watanabe lost an estimated $127 million while gambling in Las Vegas casinos over the course of seven years.

7. British hedge fund manager Edward Thorp is said to have lost $10 million playing blackjack in just one night in Las Vegas.

8. American football player Art Schlichter famously lost millions of dollars gambling on sports, eventually landing himself in prison.

9. New York real estate developer Steve Wynn is rumored to have lost $25 million playing craps in just a few hours.

10. And finally, the biggest loser of them all may be Japanese businessman Akio Kashiwagi, who is said to have lost upwards of $200 million gambling on baccarat and other casino games.