Does Betting Every Underdog in March Madness Work?

Betting on every underdog in March Madness sounds like a crazy idea, but there might be something to it! The NCAA Division I Tournament is known for its wild nature, so it’s an interesting plan worth considering.

I’ve tested this approach in the past two years, with 2024 showing some promise before 2025 completely destroyed my bankroll! Still, this was one of the worst years ever for betting on underdogs, and I’m not ready to call it quits yet.

I will test this approach again in 2026 by betting on all underdogs during March Madness, so stay tuned! I will only back moneyline wins this year to keep it simple. I will be adding all my picks and tracking my results in this post, starting from the First Four, so if you’re interested, make sure to visit after each round. Here’s the latest summary:

Also, adding some ground rules would be helpful, so let’s start there.

Betting Every March Madness Underdog – The Rules

Backing all underdogs during March Madness is going to be a crazy adventure, so I want to bring at least some order to this strategy. Before I explain what I plan to do, let’s just warn to avoid this if you’re doing March Madness bracket challenges. With that in mind, here’s what I intend to do.

Rule 3: Line Shopping

Using a single sportsbook for underdog betting would be very limiting, so I will use multiple March Madness betting sites. At the same time, I want to keep it fairly simple and easy to replicate for a regular college basketball fan.

That’s why I decided to limit the number to three bookmakers: Bovada, BetUS, and BetOnline. They are my favorite US sportsbooks and consistently deliver high odds, as well as cool March Madness bonuses and promos.

I won’t use any offers, though, I want to see how this works without any extra help. I will simply check the bookies and get the best March Madness odds and lines for the purpose of my approach.

Want a complete guide on March Madness betting strategies? Check out our full March Madness betting guide.

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Moneyline Betting on All March Madness Underdogs in 2026

I’ve added two underdog bets for the First Four, but the other two don’t have a clear favorite, so you won’t find them in the table below. I will keep monitoring the odds in case that changes.

Also, I’ve added all round 1 underdogs to the table, except for the two that are still waiting for the First Four to finish. One interesting find was that the discrepancy between the different bookies for the biggest underdogs can be insane.

For example, Long Island was around +2000 in two bookies, but I got +4000 at BetOnline. Goes to show how important line shopping is for this strategy!

Update After the First Four: the start has been great this year, with both First Four games that met my criteria hitting! I’m over $400 ahead so far, but it’s early days, so let’s see what happens in round one.

Update on March 20: So far, so good! Thanks a to solid upset by High Point and five smaller ones on day 1, we’re still ahead. In fact, we’ve added a bit to the profits of the First Four, and currently stand on +$432. Good signs that betting all underdogs will be better in 2026 compared to last year, but it’s still early.

Update on March 21: The second day of March Madness was brutal, with all 16 bets losing! Multiple big underdogs came close but ultimately failed to upset the odds, so I’m more than $1,000 behind at this point. Let’s hope our luck changes with the second round.

Update on March 23: The second round was rough, with one big upset coming from Iowa and a few small ones. The strategy is still significantly behind, so let’s see if the Sweet 16 can change anything. I will add all games from that round on Tuesday.

Update on March 26: All games from the Sweet 16 have been added, so let’s hope we have better luck than the opening two rounds!

Update on March 27: The first four games from the Sweet delivered two upsets, and another one was really close. Let’s hope the next four do well, too. I will add all games from the Elite 8 tomorrow.

Update on March 28: The Sweet 16 was around the break-even mark after all, meaning the system is still significantly behind. I’ve added the Elite 8 games, so let’s see how this goes.

Update on March 30: The Elite 8 as also a losing round for the underdog betting strategy, despite UConn’s insane comeback against Duke. With only three matches left, it’s obvious the strategy will once again lose money in 2026, but let’s see how much exactly.

Update on April 7: It’s been another rough year for the March Madness underdog betting strategy after I lost almost $1,800. I will be back next year to try again, either using the same approach or adjusting the system to add extra selection criteria.

March Madness Underdog Betting from 2025 Summary

Here’s what happened when I bet on all March Madness underdogs in 2025.

Note: The March Madness 2025 final was one of the games excluded from this experiment because there was no clear underdog (odds of +100 or higher).

March Madness Underdog Betting from 2024 Summary

Here’s a full timeline with my comments and results summary of my March Madness underdog betting experiment in 2025. In that year, I actually targeted both spreads and moneylines.

Final Thoughts

I feel obliged to share some predictions and a warning for this March Madness underdog betting experiment. For a start, please, gamble responsibly if you decide to follow me and bet on all March Madness underdogs this year. It’s a tricky system that could easily go wrong, so don’t risk money you can’t afford to lose!

My expectations last year were to lose money from the spreads and win from the moneylines, which is exactly what happened. This is why we will only target the moneylines in 2026.

We’ll see what happens, and I promise to analyze the results thoroughly when the tournament is over. Good luck to everyone on your March Madness underdog betting in 2026!