Betting on the Underdog: When It’s Smart, and When It’s Just a Waste of Money

Most people don’t bet on underdogs. And why would they? The favourite is the favourite for a reason. Statistics, experts, odds — everything points to them winning. But every now and then, the underdog flips the script and turns a $50 bet into a massive payday.

I have been on both sides of this. I’ve taken insane wins that made me feel like a genius and watched my underdog pick get destroyed while wondering why I even bothered. So, is betting on the underdog a strategy or just wishful thinking? Let’s get into it.

What Does It Mean to Bet on the Underdog?

This isn’t complicated — it’s betting against the prediction. The underdog is the team or player sportsbooks expect to lose. Because of that, they offer higher odds to attract some action on both sides of a bet.

It sounds easy, but here’s where people mess up:

• They think bigger odds = better bet.
• They ignore matchups, game conditions, and real strategy.
• They fall for hype instead of actual probability.

Sometimes, an underdog should be a heavy underdog. Other times, the odds are off, and that’s where insight comes in.

Why People Ignore Underdogs (And Why You Shouldn’t Always Follow the Crowd)

People love safety. Favourites are comfortable. Betting on a team that’s “supposed to win” feels smart, even when it isn’t.

The problem? Public perception skews the odds.

• Overrated teams get inflated odds. If a team is hyped up, sportsbooks adjust, and the underdog gets extra value.
• Casual bettors don’t check variables — injuries, travel fatigue, playing styles — these things get ignored.
• People chase wins, not value. The goal isn’t to win every bet; it’s to win profitable bets through evaluation and wise decision–making.

I’ve seen underdogs win because the favourite had no business being that preferred. That’s what you need the analysis — not just of the teams, but the patterns in how odds are set.

The Psychology of Sports Betting on Underdogs

This is where things get messy. Betting isn’t just numbers — it’s how your brain’s dynamics trick you.

• The “Big Win” Fantasy – You see a crazy underdog bet hit, and suddenly every underdog looks tempting. That’s not tactics — it’s just hope.
• Fear of Looking Stupid – If you bet on an underdog and lose, you feel silly. If you bet on the favourite and lose, it’s just bad luck. A classic mental behaviour trap.
• Chasing a Pattern That Doesn’t Exist – Just because an underdog won last time doesn’t mean this one will. That’s lousy methodology.

To win at underdog betting, you have to shut emotions off. Treat it like a math problem, not a gut feeling.

Underdog Betting Strategy: When to Take the Shot

Betting on underdogs isn’t about picking random long shots. It’s about finding value in odds that don’t make sense.

1. Moneyline Betting – All or Nothing

It’s simple. If the underdog wins, you win big. If they lose, you get nothing.

Best for:

• Games where the underdog actually has a shot (not just wishful thinking).
• Teams with momentum but undervalued odds (winning streaks but still disrespected).
• Situations where the favourite is overrated (overhyped media darlings).

2. Spread Betting – The Safer Underdog Play

The underdog doesn’t have to win — they just need to lose by less than the spread.

Best for:

• Teams with strong defences (keeping it close).
• Rivalry games (underdogs show up big).
• Situations where the public is blindly backing the favourite.

3. Over/Under Betting – Forget the Winner

Sometimes, the best bet is on total points. If an underdog plays a fast, aggressive offence, the Over might be brilliant. If they slow the game down, the Under could be gold.

4. Prop Betting – Betting on Individual Players

Underdog teams lose all the time. But their best players still perform. That’s why prop bets can work in your favour.

• A QB to throw 250+ yards even if the team loses.
• A striker to score even if his team gets crushed.
• A basketball player to hit 4+ threes, regardless of the final score.

This is betting on performance, not outcomes.

5. Picking the Right Time to Bet on an Underdog

Betting early vs. late matters.

• Early bets – Before the public money floods in, the odds are better.
• Live betting – If an underdog starts strong, their odds shift.
• Late adjustments – Injuries, game-day weather — these change everything.

Smart bettors don’t just bet underdogs for fun. They bet when the underdog betting odds are wrong.

Case Studies: When Underdogs Shook Up Betting Market

Leicester City Winning the Premier League – 5000-1 Odds

Nobody saw this coming. It’s one of the biggest underdog wins ever. Some fans who put down small bets walked away with life-changing money. Those who had the expertise to recognise Leicester’s momentum early made history.

Buster Douglas KO’s Mike Tyson – 42-1 Odds

Tyson was unbeatable. Until he wasn’t. A $100 bet on Douglas turned into $4,200.

Super Bowl Upsets – Giants Over Patriots (Twice)

Both times, nobody believed in the Giants. Both times, they won outright — and people who bet on them cashed in big.

The Betting Risks of Betting on Underdogs (Because It’s Not Always Smart)

Betting underdogs can drain your bankroll fast if you’re not careful.

• Not every big odds bet is worth taking. Some teams are bad for a reason.
• Favorites win for a reason. You can’t just bet against them because you want an upset.
• Chasing underdogs can get expensive. Winning less often means you need higher payouts to balance your losses.

What the Experts Say About Betting on Underdogs

Sharps don’t just bet on underdogs for fun. They:

• Track line movement to see where the sharp money is going.
• Find overvalued favourites and bet against them.
• Check historical trends and team matchups instead of just odds.

How to Start Betting on Underdogs (Without Going Broke)

• Start small. Bankroll management is everything.
• Track your bets. Learn from wins and losses.
• Look at stats, not your emotions. Betting is math, not magic.

Disclaimer: The content provided on this page, including all predictions, odds, and related information, is for entertainment and informational purposes only. While we strive to ensure accuracy and timeliness, we do not guarantee the correctness or reliability of any predictions, data, or information presented here.