Betting on the Underdog: When and Why It Pays Off in 2025

Written by: Stefan Jonsson | July 31, 2025
Venus Williams

Betting on underdogs can be a thrilling high-reward strategy in 2025, offering value when odds misjudge potential.

With recent upsets in tennis, basketball and other sports, experienced bettors are finding opportunities where undervalued players or teams defy expectations. But where and why does it really work?

Venus Williams stunning 6-3, 6-4 victory over Peyton Stearns on July 22nd, at the Mubadala Citi DC Open is a prime case of good value in a tennis bet. At 45, ranked No. 305, she was a +500 underdog against the No. 35 Stearns, who led 4-2 in the second set. Williams 28 winners and 65% first-serve win rate turned the tide, paying out handsomely for those who backed her experience. Of course, it’s difficult to spot these as we don’t know everything about the players but there are often signs to look for, something we try do in our own predictions.

Basketball is another sport with upsets quite regularly and it’s showing in many experts NBA picks lately, where bettors want to find value and bigger wins. In basketball, the Detroit Pistons upset of the Boston Celtics in February earlier this year, stands out as a significant victory at high odds. Led by Cade Cunningham’s 21 points and 11 assists, the Pistons defeated the defending champions 117-97. Despite being underdogs, Detroit showed efficient shooting and strong team play, with contributions from Malik Beasley’s 26 points, overcoming the Celtics formidable lineup.

Underdog bets pay off when public bias inflates the favorites odds or smaller injuries weaken the top teams. The key is spotting value: look for players or teams with recent form upticks (e.g., Williams July 21 doubles win) or matchups favoring their strengths.

A good tip is to always analyze head-to-head records, like Williams 6-2 edge over Stearns error-prone style, or team stats like Pistons record against ranked foes. This is a quick way of seeing if there are chances for an upset for a specific match. Check betting lines for discrepancies, odds of +300 or higher often signal undervaluation, and monitor live odds shifts for late value. Note though that these odds can shift of different reasons, it can also be a way for the bookies to balance their risk if they get a lot of money on one player or team. Tools like the Kelly Criterion can help manage risk, balancing stake size with perceived edge.

Williams +500 payout and Pistons strong return prove underdog betting’s allure, but it’s not blind luck, her 85% hard-court win rate and Pistons shooting edge were clues and those were just a few of them. Spotting undervalued bets requires digging into stats over hype, though the volatility keeps it a high-stakes thrill. Focus on mid-tier tournaments or early rounds for the best odds and chances of finding the next big odds win.

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Stefan Jonsson

Stefan is a writer at Tennisnerd since 2023 and keep the readers updated on new events, betting tips and general tennis news.