Winning on Underdog Fantasy is hard. We broke down the math for how to win Underdog Pick’ems, including all the odds and payouts you should know to be profitable on the platform. However, it can be tough to find two or more picks with positive expected value (EV) to build out a card. But every now and then, Underdog will put out a free square, or as they call it, a “pick’em special.” When they do, you’ll definitely want to jump on the opportunity. That leads to an obvious question, though: What is Underdog Fantasy free squares? So, let’s do a little Underdog Fantasy Pick’em Free Squares explained post, eh?
So, when are free squares available on Underdog, and how often? Is there a catch to them?
Free squares aren’t rocket science. They are promotional offers for big games like the Super Bowl or special events like the NBA Finals where one bet is reduced to a number that is almost impossible to lose. Think Tom Brady over/under 0.5 passing yards or Nikola Jokic over/under 0.5 points. Underdog’s free squares are can’t-miss attachments to your pick’em board whenever they’re available.
Successful play on Underdog requires some knowledge of sports and of probability. Access to tools like Portfolio EV’s Underdog tool can help you maximize your knowledge. With the right tools, projections and a bit of know-how, free squares can become a key piece of a winning strategy on Underdog.
Stokastic is taking its elite projections to the pick’em game! With the Pick’em package, you’ll unlock powerful tools like the PrizePicks Optimizer, Underdog Optimizer and DraftKings Pick6 Optimizer, helping you build +EV entries in just a few clicks. Whether you’re a seasoned pick’em player or a newcomer, Stokastic’s Pick’em tools give you a winning edge.
Underdog Pick’em Free Squares Explained: What is Underdog Fantasy Free Squares
Nothing is ever guaranteed, especially not in sports. Although we can almost guarantee that Tom Brady will throw a one-yard pass or that Nikola Jokic will put a shot in the net, weird things happen — but rarely enough for these to be virtual locks. Once we have a free square, the rest of the Underdog calculation becomes a lot easier. Frankly, anything you attach to that free square will have a positive ROI in the long run.
The two-pick pick’em multiplier on Underdog pays out three times your money. You typically need both of the legs to hit at 58% of the time on average in order to break even. That is equivalent to two bets of -137 or better without accounting for the vig. With a sportsbook’s hold, you need to find two bets that average a -154 vig. We already broke this down for every pick’em option on Underdog, and you can read about it here.
The free square changes everything. On a two-leg multiplier pick’em, you’ll only need a pick that cashes north of 33.3% of the time. It’s hard to find a pick with worse odds than that, and if you manage to do so, the opposite side will be a winner 66.7% of the time.
However, not all of Underdog’s multipliers are created equal. The varying payout structure means that the picks you do need to hit will have different probabilities, even if you’re getting that free square. Keep these percentages in mind so that you can make the most of the promo.
Here are the win odds that each of your bets will need when you use a free square. Following these breakeven points will guarantee you have a positive long-run expectation with the promo. Underdog has pick’em card sizes of two, three, four and five legs, but since we’re counting one leg as a lock, the probabilities below reflect the number of non-free square bets you’ll have on your card. The two-pick multiplier is one, the three-pick is two, and so on.
| Play Type | # of Picks | Payout | Minimum Total Probability for Cashing | Average Implied Odds To Break Even for Each Pick | American Odds Needed to Break Even for Each Pick | American Odds Needed to Break Even for Each Pick (Standard Vig of 4.76% Included) |
| Multiplier | 1 | 3x | 33.3% | 33.3% | +200 | +203 |
| 2 | 6x | 16.7% | 40.8% | +145 | +157 | |
| 3 | 10x | 10% | 46.5% | +115 | +126 | |
| 4 | 20x | 5% | 47.3% | +112 | +122 |
You probably noticed a trend in the numbers. The lower the payout, the easier it is to win. If you’re getting a free square on a two-pick card, then you only have to find one bet with a 33.3% chance of hitting to make it +EV. It gets a bit more difficult after that. Three-pick cards — or two picks plus the freebie — need the bets to average a win probability of 40.8%. That’s doable, but it does introduce some variance because you’ll have to connect on two more bets. Nevertheless, tools like Portfolio EV market-based betting model will help you find those 40 percenters easily.
Things do get tougher from there. The four-pick card requires the bets to have an average win probability of 46.5% or higher. It goes to 47.3% on the five-pick card, which is the largest you can play on Underdog Fantasy.
All these win odds are much lighter than you would need without the free square. We calculated those already, and they’re worth reviewing. There are two important takeaways. First, as long as you are finding bets with a win probability over 48%, you will have a positive expectation with any multiplier card size if you use a free square, or pick’em special.
Second, the odds you will need for each bet will increase as your card gets bigger. Those odds are creeping closer to what you’ll need on a regular card without the freebie promo. For example, a five-pick card without a free square requires the bets to average a 54.9% hit rate. That’s high, but not compared to the gap you will see in a two-pick or three-pick multiplier.
Now that you have these numbers you can easily take advantage of the Free Squares on Underdog. Be on the lookout, because they’re offered on rare occasions. There are also a couple of caveats that you should be familiar with.
Check out Portfolio EV tools for winning Underdog Fantasy Pick’em plays that are updated every day. Subscribe to Portfolio EV to gain full access. If you want to learn more about Underdog Fantasy Pick’em, check out our guide, see if it’s legal in your state — or check out our breakdown of their Free Squares promotion. Haven’t signed up yet? That’s great — new users can get their first deposit matched up to $1,000!
Be Mindful of Percentages and Playthrough on Underdog Fantasy
After all the buzz about win probabilities and how much easier it is with free squares, there is a need for a disclaimer. A free square is not a literal lock. Nothing in sports betting is. There’s that one-in-a-million chance that Nikola Jokic slips on his shoelace in the first minute of the Denver Nuggets game, hits the bench and never comes back to score a bucket. The same can happen to Tom Brady too. So while the bets are theoretical locks — trust us, you should take them– anything can happen!
You should also be mindful of the playthrough clause on Underdog. When you do hit on your free square multiplier card, you won’t be able to withdraw your winnings immediately. Anything you win above the previous multiplier level will need to be wagered once more (1x playthrough) before you can access the funds.
In other words, if you hit a five-pick pick’em entry that had one free square, you can cash out for the amount the ticket would have paid on a four-pick card. Your account will be credited for the whole five-pick 20x payout, but you will need to wager everything on top of the original four-pick amount to be able to withdraw it. In that sense, the free square isn’t completely free. You’ll have to stay on the site a bit longer.
There’s never any such thing as a free lunch. However, you will see the money eventually and be able to withdraw once you play through it once. The key is to play through and win. You can do that by checking out Portfolio EV‘s market-based betting model and applying tools like our Underdog tool to ensure a positive outcome.
