Where to Win Money with the Best Free NCAA Tournament Contests


The 2019 NCAA Tournament brackets have been released and that means it’s time to start scoping out all of the March Madness contests from around the web.

I have a combination of free contests and ones that require a deposit into an online sportsbook to enter. The sportsbooks tend to give out some pretty great prizes, and the entry fee is just a deposit into an account to wager with and isn’t used on the entry.

When entering into these contests, you can either fill one bracket out to use in all of them, or you can mix and match.

If you happen to do really well and submit the same one to each, it could make for an interesting beginning of April if you cash in at multiple places!

I’ll keep this list updated as I learn about more contests this year, but if you have any suggestions just shoot me an email and I’ll get it posted.

Remember to bookmark this page and send it to your friends, family, or anyone else who will be interested in filling out brackets this year. Why not help them enter free contests to earn some money?

Also, be sure to check out my bracket to see my Final Four picks and National Champion.

Top Online March Madness Tournament Challenges 2019


ESPN is one of the easiest and most popular brackets to fill out. Their grand prizes this year are trips to the Diamond Head Classic in Hawaii and a trip up to the ESPN campus in Bristol, CT for a tour of their facilities.  Because they have so many entries, the top percentage of brackets are placed in a pool and winners drawn at random. This makes it one of the most difficult to win, but also gives you pretty amazing bragging rights if you manage to submit one of their best brackets.


Yahoo’s contest offers a $1,000,000 prize to the best bracket this year. You can enter up to ten times. This is probably the most straight-forward and biggest prize you’ll find for a free entry, but there will be some massive competition so make sure to bring your ‘A’ game!

CBS Sports

As an official bracket partner of the NCAA Tournament, CBS is offering an all-expenses paid trip to the 2020 Final Four.  The Prize includes four tickets to the semi-finals and finals, plus $6,000 in cash for luxury hotel accommodations and airfare.

In addition to the traditional bracket, CBS also has a “round-by-round” contest, where six people get a chance to score tickets to next year’s Final Four (semi finals and finals), but just $500 of expenses paid for.

PYOChallenge (Pour Yourself Out)

* 1st Place- Two NCAA Championship tickets with lodging
* 2nd Place– unlimited Chick-fil-A for you & your family for the entire month of May
* 3rd Place– unlimited pizza for you & your family for the entire month of May
* 4th Place– unlimited ice cream for you & your family for the entire month of May
* 5th Place– unlimited coffee for you & your family for the entire month of May
* 6th-17th Place– DudePerfect official basketball (retail $39.99)

Free to enter, optional donations go to a great cause.

Jiffy Tickets

Another straightforward contest comes from Jimmy Tickets.  Just score the most points and claim your prize!  All prizes are paid out in gift cards:  $1,000 for first, $500 for second, $300 for third, and fourth through tenth places all get $100.

Paid March Madness Bracket Pools With Huge Prizes


Thinking about picking a perfect bracket this year?  5Dimes is where you want to enter that bracket!  This online sportsbook does collect an entry fee for their contests, however, the prizes are well-worth it if you happen to pick perfection.

5Dimes will also hosts a number of pools with 100% payouts to the top brackets, the more entries, the more you stand to win!


You will need an account and a $100 deposit (or more) to enter Bookmaker’s Perfect Bracket Challenge.  Once you’ve signed up, you’ll be eligible for the grand prize $1 million perfect bracket payout.  Even if you fall short of filling out everything correctly, there are still some great prizes to be won.  First place takes home $10,000 in cash, second gets $5,000, and third is paid $2,500.  All entries receive additional loyalty BetPoints to their account based on where they finish!


BetOnline is putting up $10,000 in cash prizes for their Bracket Madness contest.  Top prize is $3,500 with second through fifth receiving $2,500, $2,000, $1,500, and $500, respectively.  To enter, you’ll need a BetOnline account with at least $50 of real money wagered in each of the three weeks of the tournament.


WagerWeb brings back their $1,000,000 Mayhem contest, which has a bit of a different spin.  Instead of simply filling out a bracket, each team is assigned a point value and the most points accumulated at the end of the tournament wins the contest.  Be sure to check the details out on eligibility for this one as soon as the information is available!

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