The NCAA Tournament field is set!  Millions will take part in office pools this season.  We have tracked down the top online March Madness contests with the best prizes. Most are free to join!

List of 2019 March Madness Bracket Challenges to Fill Out & Prizes

Yahoo Sports

If you enter just one bracket challenge this year, do yourself a favor and submit it at Yahoo. This year’s challenge is known referred to as the  “Best Bracket Millionaire.” No more pick a perfect bracket and win at million bucks. Simply finish with the best score on Yahoo’s site and receive a check for $1,000,000.


ESPN’s Tournament Challenge gives you a chance to win a a trip for two to the 2019 Maui Invitational. That includes roundtrip airfare, 5 night hotel accommodations and tickets to all sessions. On top of that, they throw in a $10,000 gift card.

There is one downside to this challenge. The grand prize does not go to the contestant with the highest score. There will be a random drawing from top 1% of all entrants to determine the winner.

CBS Sports

Compete in CBS Sports Bracket Challenge for a Final Four package worth $10,000. The winner gets 4 tickets to the 2020 Final Four games (semifinals and championship). As well as $6,000 cash for hotel/airfare. Like ESPN, the top bracket doesn’t guarantee you the prize. CBS takes the top 10% of all submissions and selects the grand prize winner at random.

Fox Sports/Sports Illustrated

Win the “Cousin Sal Bets the House Bracket Challenge” and take home a check for $10,000. While that’s just a fraction of what Yahoo is offering for their winner, pick a perfect bracket and you will get the keys to ‘Cousin Sal’s house in Manhattan Beach, California. For those wondering, the house is estimated to be worth $4.5 million.

The official site of college sports is in on the action. Enter the “Capital One NCAA March Madness Bracket Challenge” and compete for some cool prizes.

USA Today

Find out if you have what it takes to earn the title “Office Champ” by entering the USA Today pool. Not the best of prizes, but USA Today is expected to hand out five $1,000 Visa gift cards in a random drawing for those top participants that qualify.

Jiffy Tickets

Jiffy Tickets is definitely one I recommend taking part in. They pay out in gift cards of your choice (great selection) for the top ten finishers in their contest.

  • 1st Place: $1,000
  • 2nd Place: $500
  • 3rd Place: $300
  • 4th-10th Place: $100

Alumni Hall

Looking for some new apparel to support your favorite team? Join the Alumni Hall Bracket Challenge. They are giving away gift card (to their site) to the top 10 contestants.

Bokampers Bracket

A perfect bracket in this contest will net you $1,000,000. Anyone who can get 60+ games right will receive $25,000 in cash. If neither of those are hit, the bracket champion will take home a 60″ HDTV, while 2nd place gets a $200 gift card.


Win cash by taking down the top spot in the March Mandet Challenge. Unlike other contests, they offer you a chance to redeem yourself if you get off to a bad start.

Old Chicago

Finish with the highest score in the Old Chicago contest and win a trip for two to the 1st and 2nd rounds of the 2010 NCAA Tournament. Includes round-trip airfare, hotel accommodations and a $500 visa.

March Fever

March Fever is giving away some serious cash to anyone who can own the bracket this year. Get every game right and walk away with $1,00,000. Get 61 or 62 games correct and take home $10,000.


This fantasy sports site is offering up $5,000 to anyone who gets within 1% of the best possible score.

The PantaGraph

Enter of a chance to win a La-Z-Boy Kennedy Sofa

NBC Sports Washington

Grand prize for this bracket challenge is a 3-night trip for four to Universal Orlando Rest. Includes roundtrip airfare, hotel accommodations, admission to Universal Studios, Island of Adventures and Volcano Bay Water Park, as well as tickets to see the Blue Man Group.

Top Online Sportsbooks NCAA Tournament Money Contests & Pool Payouts


This sportsbook offers some serious cash for anyone who picks a perfect bracket. The prize depends on what size pool you decide to join ($1, $5, $10 or $25). Anyone who plays in their $25 pool and picks a perfect bracket will receive a cool $25 million.

A perfect bracket pays $10 million in their $10 pool, $5 million in their $5 pool, and $1 million in their $1 pool. All you need is a 5Dimes account to get in on the action.

They are paying out 100% of all prize money for each pool and there’s no limit on the number of brackets you can fill out!


Bookmaker returns their $1 million perfect bracket contest for 2016.  If nobody is perfect, they are also paying out a grand prize of $10,000 cash.  Second place gets $5,000 and third takes $2,000.  Not bad!

You must have a Bookmaker account to enter.  You will receive one entry to the contest for every $100 deposited.


BetOnline users can’t pass up on their bracket contest. If you create a new account you can get up to $1,000 in a free play bonus!  They are also bringing back the Bracket Challenge from last season.  This contest features a $10,000 guaranteed prize pool ($3,500 to the winner)!

This year they are also giving an extra $1,000 to anyone who picks all Final Four teams.  You must have an account to enter.  Gain entry by placing a wager of $25 or more.


WagerWeb offers $1 million to anyone with a perfect bracket this year.  They are also paying the top 100 brackets.  Prizes range from $5,000 to the winner to $10 for 51st through 100th place.

Win Your Contest