The 2016 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.


ESPN is giving away a $10,000 Amazon gift card and a trip for two to the 2016 Maui Invitational in its Tournament Challenge.

Unfortunately, the $10,000 does not go to the highest score.  There will be a drawing from the top 1% of entrants, and the name that’s picked will get the prize.


Yahoo’s Best Bracket Pool offers you a chance to finish with the top bracket and win $50,000 cash.

Their Celebrity Pools are also back this year.  You can get in with different celebrities and win different prizes.  Chris Paul’s pool is giving the winner a 65 inch TV.

FOX Sports

FOX is giving away a 60-inch smart TV to the winner.  The consolation prizes aren’t bad, either, as the four runner-ups get a 50 inch smart TV.

CBS Sports

Get in the top 10% of entrants and be included for a drawing to win a Final Four Package valued at $10,000.

Athlon Sports

The first place prize from Athlon will be a 60 inch LED smart TV.  Second place takes on a 32 GB Apple TV, and third place will get a $75 gift card.

Jiffy Tickets

If you finish in the Top 10 at Jiffy, you will be taking home a gift card of your choice.  First gets $1,000, second $500, third $300 and the 4th-10th place finishers get $100 each.

Sports Illustrated & Kizzang

This year, Sports Illustrated is joining Kizzang to offer a whopping $25 million price for a perfect bracket.  Top 10 finishers will also earn cash prizes.


This is the place to go if you’re trying to pick a perfect bracket.  You have get to into pools of $1, $5, $10 or $25 entries to be eligible.

A perfect bracket in the $25 pool pays $25 million.  The $10 pool pays $10 million, $5 pool $5 million, and $1 pool $1 million.

Plus, you have a chance to win real cash even without a perfect bracket as 5Dimes is paying out 100% of all prize money in each pool.


Bookmaker is paying out $1 million for a perfect bracket in 2016.  If there are no perfect brackets, then the highest scorer will take home $10,000 cash.  Second place earns $5,000 and third gets $2,000.

The kicker is that you have to deposit at least $100 to enter.  For every $100 you deposit, you will receive one free entry.


BetOnline’s Bracket Challenge has a $10,000 guaranteed prize pool with $3,500 going to the winner.  Plus, you can earn an extra $1,000 if you pick all Final Four teams right.

Not to mention, this is the best book in terms of sportsbook bonuses.  A new account can get you up to $1,000 in free play bonuses.


A perfect bracket at WagerWeb nets you $1 million.  But you have a good chance of taking home something as they are paying the top 100 finishers of their bracket challenge.  The winner gets $5,000.