Bracket Strategy Guide: How to Win at March Madness Pools

In our bracket strategy guide, we have articles on several topics, ranging from expectations, to how to spot bad advice, to understanding value and risk.

Corey Kispert and Gonzaga are a leading contender to win the national title (Photo by Brian Rothmuller/Icon Sportswire)

Welcome to our Bracket Strategy Guide, where we provide detailed advice on what it takes to improve your chances of winning NCAA Tournament pools.

Before we get to the meat of our analysis, here’s our resume in brief, supporting that our advice leads to real-world results:

  • Since 2017, our subscribers have reported winning over $1.7 million dollars in bracket pools, and that is with 27% of our subscribers responding. Actual winnings are projected to be much higher
  • 71% of our subscribers reported winning at least one prize in a pool they entered in 2019
  • 63% of our subscribers reported winning at least one prize in a pool they entered in 2018
  • 90% of our subscribers reported winning at least one prize in a pool they entered in 2017
  • Our picks outperformed the public on average in every single round of each of the last three tournaments, from the first round to having a higher percentage of entries picking the correct national champion each year
  • Our bracket pick technology was featured in WIRED magazine

In short, we provide premium technology and tools that give you the best chance to win your bracket pool — our NCAA Bracket Picks product.

Along with that technology, we have learned a lot about what it takes to improve your chances of winning a March Madness pool–and what not to do. This Bracket Strategy Guide summarizes some of our key findings. Here are the topics covered:

Five Signs of Terrible Bracket Picking Advice

In “Five Signs,” we go through some do’s and don’ts when it comes to bracket picking advice, including ignoring some “Not-So-Golden Rules.” We also briefly discuss things like having good objective odds, public pick popularity numbers, and why it is important to pay attention to both the size of your pool and the specific scoring methods.

Setting Expectations for Winning Bracket Pools

In this article, we discuss what your realistic expectations should be when playing in contests like March Madness pools, where there are often few prize payout slots compared to the number of entries, but the prize money if you do win can sometimes be substantial.

Why Bracket Pools are a Better Investment than the Stock Market

Bracket pools present plenty of opportunity to generate an excellent rate of return if you know what you are doing. It’s not always an efficient market. We also touch on strategies to increase your odds of realizing those returns.

Every Year is Different

One of our key tenets when providing customized advice for bracket pools: every year is different. What worked one year may not work in another, and simply blindly picking a certain number of seeds or upsets because of what has happened in the past is not the best route to giving yourself a chance each year. In this article, we dig deeper into some of the examples and situations that are simulations have revealed over the years.

The Danger of Picking Too Many Upsets

One of the biggest mistakes most bracket contestants make: picking too many upsets. We go through some of the reasons why this is the case, and also provide concrete examples from recent tournaments. This includes a discussion of the upset-filled 2018 tournament, where Loyola-Chicago went to the Final Four.

Balancing Risk and Value in Your Bracket

In this article, we dig deeper on the two competing considerations when filling out your bracket: finding values, and properly assessing risk. We also discuss the impact of your pool size, when it comes to the proper balance of these two factors.

Bracket Pool Scoring Systems: Why They Matter and How to Exploit Them

The scoring system used in your pool should absolutely drive your strategy. We go through some common scoring systems and some fo the pros and cons, and also provide some advice on how to adapt to each.

March Madness Myths

Our March Madness Myths series, which serves as an Appendix to the Bracket Strategy Guide. In it, we discuss some “myths” that come up when it comes to the NCAA Tournament and picking in bracket pools.

  • Myth: Past Performance Matters: In this article, we look at pick popularity based on how teams did in the previous tournament versus expectations, and show that performance the next year doesn’t seem impacted by recent past performance, but value and popularity does.
  • Myth: You Can’t Pick All Number 1 Seeds: A large percentage of the public is averse to picking too many No. 1 seeds. We break down why you shouldn’t fall for that myth and should make your picks each year based on the specifics of that tournament.
  • Myth: It’s All Random: In this myth article, we push back against a recent strain of popular advice that tells people the results are random and hard to predict.
  • Myth: Your Bracket Should Match Historical Trends: It seems like a lot of people try to submit brackets that match historical trends for how often certain results happen, from picking upsets like 12 over 5, to the number of teams below a 2 seed to the Final Four. We push back against the idea that this is optimal strategy.

Tournament Years In Review and Past Tournament Content

If you want to see how our advice in specific recent tournaments played out, you can read our years in review, and also see the actual write-ups that we provided to subscribers before the tournament began.

2019

2018

2017