Ranking the Best March Madness Bracket Challenges from oddschecker, ESPN, bet365 and More

Ranking the Best March Madness Bracket Challenges from oddschecker, ESPN, bet365 and More

With Selection Sunday now complete and the March Madness brackets now in place, millions of basketball fans will now be looking for the best bracket challenges!

There are plenty to choose from but we're here to bring you the very best options - and ones that offer the best incentives.

You'll be able to give yourself the chance to win some big prizes over the next few weeks as March madness takes center stage, and there are some bracket challenges offering millions of dollars to the winners.

We'll bring you all the details on bracket challenges from the likes of bet365, ESPN, and of course oddschecker, as you could win big by making a series of selections before the tournament gets underway.

bet365 Bracket Challenge: Win up to $10 Million on March Madness

The bet365 bracket challenge for March Madness gives users the chance to win up to $10 million by selecting the perfect bracket!

The chances of selecting the perfect bracket are slim, but not impossible - so that is why bet365 is also offering $100,000 to the player that picks up the most points for their picks, even without a perfect bracket!

Find out details on how you can enter the bet365 bracket challenge here:

Step 1: Click this link to go straight to the Bet365 registration page for the $10 million bracket challenge.

Step 2: Sign up for an account if you haven't already, following the steps outlined by Bet365.

Step 3: Enter your bracket predictions!

Even if you don’t land a perfect bracket, you could still walk away with up to $100,000 for having the best bracket in the challenge!

oddschecker March Madness Bracket Challenge: Win Up to $500 in Prizes

Here at oddschecker, we're mad about March Madness which is why we created a bracket challenge for 2025!

Enter your selections for a chance to win up to $500 in prizes by entering this free-to-play bracket challenge and put your college basketball knowledge to the test!

The prize structure for the oddschecker Bracket Challenge is as follows:

• Grand Prize: $500 Fanatics gift card for the highest overall bracket score.
• Runner-Up Prize: $75 Fanatics gift card for the second-place finisher.
• Top Performers: $25 Fanatics gift card for the top 10 overall finishers.
• Best Underdog Picker: $25 Fanatics gift card for the bracket with the most upset victories.

Sign up now and start making your picks!

DraftKings' March Mania Bracket Challenge: Win up to $1M in prizes

DraftKings hosts plenty of March Madness contests where participants make selections based on the format. The contest structure and prizes depend on which pool you choose, but the general format involves making picks before each round and accumulating points based on correct selections.

Most of these contest formats are your standard bracket contest or survivor style.

To enter:

1. Sign Up for a DraftKings Account – If you don’t have one, create a free or paid account.
2. Join the March Mania Picks Contest – Navigate to the promotions or contest section on DraftKings to enter.
3. Find a pool that you are interested in joining
4. Make Your Picks – Choose winners for individual matchups, prop bets, or other game-related predictions.
5. Submit and Track Progress – Follow your picks throughout the tournament to see how you rank against other participants.

ESPN Bracket Challenge: Win up to $135,000 in prizes

ESPN also have a bracket challenge for March Madness where users can win up to $135,000 in prizes for selecting a perfect bracket!

You can play against your friends and ESPN personalities to compete for the best bracket and bragging rights in 2025!

It's free-to-play and players can win up to $135,000 in prizes, so find out how to enter below:

Step 1: Go to the ESPN Bracket Challenge page and sign up

Step 2: Click on the 'Create a Bracket' button to get started. You can create up to 25 brackets to give yourself the best chance!

Step 3: Create groups to play with friends. Click on the 'Groups' tab and you'll see buttons to both create new groups and join existing ones

That's it! Make sure your picks are in by 12:15pm ET on Thu, March 20th which is when the brackets will lock!

Correctly select the National Champion to be eligible to win a grand prize. Additionally, fill out 25 brackets to be eligible to win a first prize! Group Creators that create a group with 10+ entrants will be eligible to win a group creator prize!

Men's Tournament Challenge: Twenty (20) $5,000 grand prizes + Twenty Five (25) $1,000 first prizes + One $10,000 group creator prize

2025 March Madness Schedule

Here is when the March Madness tournament games will be played over the next few weeks:

• Selection Sunday: 6 p.m. ET Sunday, March 16
• First Four: March 18-19
• First round: March 20-21
• Second round: March 22-23
• Sweet 16: March 27-28
• Elite Eight: March 29-30
• Final Four: April 5 at the Alamodome in San Antonio, Texas
• NCAA championship game: April 7 at the Alamodome in San Antonio, Texas