Beginner’s Guide to Player Prop Pick ‘Ems on Underdog

by Ahaan Rungta · Fantasy Football

This is the Beginner’s Guide to Player Prop Pick ‘Ems on Underdog! Is sports betting not legalized in your state? Or maybe you just want to find an edge on the player prop market after reading Seth Diewold’s guide to prop betting? DFS sites like Underdog Fantasy provide the luxury of playing player prop over/unders, removing the complexity of having to predict higher-variance outcomes like game results and touchdowns. The idea is simple: pick your favorite two to five player props on the sports slate (either overs or unders). If you’re correct on them all, you profit an amount depending on how many selections (legs) were in your entry.

In this article, I’ll outline how to approach pick ‘ems, particularly in the NFL, so that you can construct winning pick ‘em entries like we do in the Underdog Pick Generator and in my article series containing my favorite pick ‘em props of each week. If you find this article useful, and are drawn to playing player prop pick ‘ems, you can either play your own favorites or tail ours on Underdog Fantasy’s pick ‘em menu. Upon entry, use promo code UNDERWORLD for a 100-percent deposit match up to $100.

Rules: The Basics of a Pick ‘Em Entry

It’s important to realize throughout the process of finding value that Underdog Fantasy is a business that needs to profit in the long-term. Therefore, it’s important to understand the nuances in the rules of pick ‘em so that you can find value as often as possible and stay away from traps.

Entry Logistics

  • Every entry must have either two, three, four, or five legs. DFS sites restrict users to a maximum of five legs so that they don’t run the risk of players hitting mega-parlays that can turn $5 into thousands with one hit. They also require at least two legs simply so that players must be correct on at least two over/under decisions to win. This is obviously a more difficult task than finding one line you like.
  • There must be at least two different teams featured in the entry. There’s a very basic reason DFS sites do this—correlation. The payout structure of an entry does not change regardless of which props you are choosing to play. Therefore, you cannot simplify an entry to two props that are directly related. For example, if you anticipate Damien Harris to be the primary back for the upcoming Patriots game, you cannot simply take his OVER on rushing attempts parlayed with the UNDER on Rhamondre Stevenson’s rushing attempts. This would be essentially one bet on the Patriots backfield at the price of a 2-legger.

Payout Structure

  • The payout structure of your entry depends on how many legs are included. There is the option of insurance for entries with at least three legs if one of your legs misses.
    • All Pick-2s pay out three times your buy in, implying a 2x profit, the equivalent of a +200 hit on a sportsbook.
    • Pick-3s with no insurance pay out six times your buy in, implying a 5x profit (+500).
      • With insurance selected, the payout would be three times your buy in (2x profit) if all three legs hit and your buy in (break even) if two of the three legs hit.
    • Pick-4s with no insurance pay out 10 times your buy in, implying a 9x profit (+900).
      • With insurance selected, the payout would be six times your buy in (5x profit) if all four legs hit and 1.5 times your buy in (0.5x profit) if three of the four legs hit.
    • Pick-5s with no insurance pay out 20 times your buy in, implying a 19x profit (+1900).
      • With insurance selected, the payout would be 10 times your buy in (9x profit) if all five legs hit and 2.5 times your buy in (1.5x profit) if four of the five legs hit.

Parlay Profitability

Parlays continue to be one of the exciting ways bettors can turn wagers into large winnings. When they hit, they look good on the track record. However, the reality of wagering any amount of money on sportsbooks and DFS sites is the platform is smart and will find ways to win off users in the long run.

Parlays are a notorious example of bettors falling for the glory of the best case scenario. It is well-documented how unprofitable it is for your bankroll to rely solely on parlays with several legs. However, in pick ‘em entries, you are parlaying between two and five legs. There are certainly ways to maximize your edge under these circumstances and win long-term.

For starters, sportsbooks are sharp in the long run. Their lines are usually ahead of the insider news and move accurately to reflect the likelihood of the events you can bet on. The reason they stay in business is they are always smarter than casual bettors. Additionally, they are on their toes at all times to move lines that will give themselves as much value as possible.

How Do You Decide Whether Your Pick ‘Em Parlay Has Profit Relative to a Sportsbook?

The idea is as follows: props that are heavily juiced as “high probability” are, in the long run, more likely to hit. Yet, you get all props available on pick ‘em sites like Underdog at the same price. For example, let’s say that in the same game, D.K. Metcalf OVER 67.5 receiving yards is set at -110 on sportsbooks (an implied probability of 52.4-percent), but D.K. Metcalf OVER 5.5 receptions is set at -140 (an implied probability of 58.3-percent).

The better play on pick ‘em is to play the receptions. You’ll notice in my article series that I often target props whose lines are extremely favorable on sportsbooks. A casual bettor might pick two props with similar odds. Perhaps, one of which is -105 on a sportsbook like FanDuel and the other at -110.

A Deeper Explanation

As a pick ‘em player, since a pick-2 earns you a 2x profit bonus, you ideally want to exceed a 33.33-percent implied probability to make the ticket a positive expected value. However, a parlay of those two props, assuming sportsbook prices of -105 and -110, would imply a bet probability of 26.8-percent. In that scenario, you’re leaving value on the table. Below, I’ve included a table of implied leg probabilities required for each leg of a pick ‘em parlay to at least hit the expected value barrier to consider the bet profitable. In this case, we are assuming you don’t use the insurance feature of Underdog. The insurance option allows fantasy gamers to sacrifice profit on a perfect ticket for cash back on a one-leg-off.

Another similar approach is to find lines that are simply different altogether than the ones offered on pick ‘em sites. I found a perfect example of this in my Week 7 pick ‘em article. This occurred when Breece Hall’s rushing + receiving yard line was set at 94.5 on a  sportsbooks but a ridiculous 12 yards lower (82.5) on Underdog. Clearly, the value here lies in the OVER on Underdog, and I pulled the trigger.

This ended up being the game where Hall tallied 72 yards on just four touches before his season-ending ACL tear in the second quarter. It didn’t cash due to the injury. However, it was clearly the right play. If he ended the game anywhere between 83 and 94 yards, that would have been a free lunch given to us by Underdog.

Takeaway 

It’s clear from the table above that the value you need from a sportsbook’s lines to make a pick ‘em entry. With no insurance, profitable differs by number of legs, so it is very much worth playing pick-3s and pick-5s. Given the payout structure of Underdog, you will more often find props that are -122 or steeper than -137 or steeper, per sportsbook prices.

In my article series on Underdog and Sleeper pick ‘ems, I often recommend mixing and matching. However, on my official card, I play entries with my top two picks on each platform. Going forward for the remainder of the season, I’ll have more pick-3s so that you can tail 3-leg entries verbatim. I feel more confident doing this since the Underdog pick generator has had a high success rate. Additionally, I feel confident because of PlayerProfiler.com’s play-by-play data and player pages from the 2022 season. These pages make it increasingly easier to read offenses and player involvement as the season progresses.

What About Insurance? Is It Worth Playing Underdog Entries With Insurance Turned on?

If you’ve been a bettor for a long time, you’ve likely had yourself a bad beat or two. Whether it be missing a prop by a few yards due to injury, as was the case with my Hall prop in Week 7, or a five-leg parlays missing by one leg. It is a natural human tendency to “play it safer” by wagering pick ‘em entries with insurance. Players do this so that even if you miss on one leg, you aren’t losing your full wager. But is this smart?

Using probabilities, we’ll approximate what the expected winnings are for each type of Underdog wager. I’ll assume here that every leg selected in your entry is equivalent to a -120 prop (a 54.55-percent hit probability). Hopefully, when you select props, you will be sharper than the lines. Bettors should use their own research and PlayerProfiler resources to buy props that are more likely to hit. However, in this long-term case study, assume every leg has that value. The table below then shows how much you will profit in expectation for a $1 entry.

Conclusion

Of course, the numbers are negative here because we are assuming that you are naively betting -120 props on your entries. Note, that it is particularly unprofitable to use the insurance option on a pick-3. If you are to play a pick-3 entry, you can simply find three props valued at -122 and blindly bet them. This is a break-even strategy in the long run. Indeed, the correct approach, if you like insurance, is to use it on a five-leg entry.

In our pick ‘em prop articles, we particularly recommend managing your entries, especially if you’re a beginner, by selecting only a small set of props. Additionally, they should use using no insurance on pick-2s or, as we discovered above, pick-3s. It’s not a bad idea to use insurance on a pick-5 entry. However, in the long-term, there isn’t a major difference between the probability of using insurance versus not using insurance on pick-5s.

I’ll close this article with three short pointers on how to profit long-term playing pick ‘ems. These bonus notes can go a long way into taking the next step from casual wagering into a smart wagerer.

3 Bonus Tips: Finding Pick ‘Em Edge

Sportsbooks and DFS sites continue to be sharper than the average sports fan. Our job is to beat their edge via research, soft lines, and staying ahead of the game as lines move. Here are three hacks to engineer the process of building for you.

No. 1: Correlated same-game UNDERs

Earlier, I mentioned that you cannot simply build a ticket out of correlated players on the same team. One of the easiest ways to play correlated props while building a valid Underdog ticket is to add in props from their opponent. For example, in Week 8, the Rams play the 49ers in a divisional game.

If you like this game to be low on offense and successful passing, you can stack this game by taking the UNDER on both quarterbacks’ passing yards and their top receivers’ receiving yards. In 2021, former PlayerProfiler Director of Analytics Josh Larky crunched the numbers on recent data. He outlined a thesis on why this has proven to be a profitable long-term strategy.

Based on our probabilities above, you might also want to add a fifth leg to your ticket. This is regardless of whether you use insurance or not. This fifth leg can be from any game. It can be either from the game you just stacked or another one. Here’s an example (for display, I am not playing this ticket verbatim).

No. 2: Discipline Your Wagers

Managing bankroll, regardless of spikes in results, and staying disciplined to what you can afford will go a long way in making the process of betting and playing DFS enjoyable. While the hits are always fun, it is simply impossible to play against the market and win every bet. The best players in the world will have cold streaks. The worst thing you can do is react abruptly to a loss and chase immediate winnings. In my pick ‘em articles, I have associated a wager size with every ticket (usually a 0.5u wager for each pick-2, for example).

In betting, a unit (denoted by a u) generally represents 1-percent of your gambling bankroll and your level of confidence in a play should be directly correlated with the wager. If you have assigned a bet as a 0.5u wager, and you lose it, don’t up your next 0.5u wager to 1u. If you watch enough sports, you know that there’s always a method for a prop to lose no matter how ridiculous the scenario might be. Don’t blow your bankroll with impulsive decisions. In the long term, profit will most likely find the mathematically-driven, not the unnecessarily brave.

No. 3: Take Advantage of Promotions and PlayerProfiler’s Resources

In the previous section, I already discussed finding advantageous lines. Part of the process in doing this, especially for NFL props where games primarily occur every Sunday, is staying ahead of a market if it’s behind on moving a line. For example, say a wide receiver’s reception line is set at 4.5 to open the market on Wednesday. In Thursday practice, a teammate wide receiver goes down due to an injury. You will likely see sportsbooks immediately adjust to this by making the OVER on 4.5 receptions much more pricey. They may even move the line to 5.5. If Underdog still has the line set at 4.5, it is likely smart to take that OVER.

Another related way of squeezing value out of soft lines is to take advantage of promotions that Underdog Fantasy often runs. For example, earlier this month, Underdog ran a free leg promo on MLB pitcher Aaron Nola where they changed the line to OVER 0.5 pitches thrown. He was guaranteed to hit this since he was the designated starter for his team’s playoff game. I took advantage by just adding my other favorite leg. Thus, I got a 1-leg play for the payout of a 2-legger.

If you haven’t already joined Underdog Fantasy to take advantage, you can do so now and start mixing multiple sports if you so choose. Upon entry, use promo code UNDERWORLD for a 100% deposit match up to $100.

Final Words

Once you join Underdog, you can start taking advantage of all the tips you learned from this article and start playing if you find props you like. Every Thursday, PlayerProfiler releases an initial set of 10 to 15 pick ‘em leans in the upcoming NFL slate, per Underdog’s lines. Those get uploaded to the Underdog Pick Generator on the DFS Dominator on the website. This year’s leans are on fire! Players who have been tailing most of the props have found themselves profitable several weeks in a row. This is another example of staying chronologically ahead of the market and snagging valuable lines while they are ripe.

On Friday, I publish my favorite pick ‘em props for my “final card” on both Underdog Fantasy and Sleeper. These get published in the “Best Pick ‘Em Player Props” article series.