Polymarket Whales Lose Millions in a Day of Premier League Upsets

Key Takeaways

Two Favorites, Two Seven-Figure Losses

The first loss came at lunchtime. Between 10:33 UTC and the 11:30 UTC kickoff at Villa Park on Oct. 24, the trader 3edmond.dantes bought 1,672,836 shares in City to win for $1,036,694, an average of about 62 cents each, on binary contracts that pay $1 if the outcome happens and nothing if it does not.

Manchester City, who had a perfect record in the Premier League up to this point of the season, despite being embroiled in financial scandal, were 60.5% favorites just before kickoff, with Villa at 18.5%.

Nicolas Jackson put Villa ahead in the sixth minute, and Erling Haaland’s header brought City level in the 52nd, pushing their price back up to about 50%. However, Jackson scored again eight minutes later, City’s chances fell to about 20% within minutes, and the scoreline remained unchanged until the end of the game—meaning 3edmond.dantes’ position finished worthless, a $1.04 million loss.

At Stamford Bridge that evening, joseph00677 bought 3,034,840 shares in Chelsea to win for $1,624,069 across 13 trades between 15:29 and 15:57 UTC, ahead of the 16:30 UTC kickoff. Chelsea were 51.5% favorites, with Tottenham, who flirted with relegation last season and remain mired in the lower half of the table, at 23.5%.

The game was goalless until the 77th minute, when an own goal by Chelsea’s Mike Penders put Spurs ahead, and Mathys Tel added a second in the 87th, leaving joseph00677 down $1.62 million.

The trader known as raybanman was on the other side of the same bet, with another massive wager. It bought about 1.6 million “No” shares on a Chelsea win at an average of about 50 cents and 225,000 Tottenham shares at about 25 cents, realizing $795,171 and $168,948, a total of about $964,000.

The loss followed a string of large football wins for the joseph00677 account, which made $1.30 million on Atlético Madrid on Oct. 13, $1.54 million on Real Madrid on Oct. 14, and $1.59 million on Arsenal on Oct. 18, against a $448,222 loss on Deportivo La Coruña in between. Even after Saturday, the account sits second on Polymarket’s monthly profit leaderboard at $5.61 million.

The trader 3edmond.dantes, who placed no other bets that day, is down $1.24 million all-time. Saturday’s two losses follow weeks of big single-game swings on Polymarket, from the $500,000 Seahawks-Broncos duel to a $147,000 Eagles bet lost to a last-second field goal.