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DFS Strategy Tips & Advice: Head-to-Head Contests

by Zachary Hanshew | @ZaktheMonster | Featured Writer
Jul 10, 2020

In the world of DFS, the two types of games you’ll encounter are Cash Games and guaranteed prize pool contests (GPPs). Cash Games are comprised of 50/50 contests and Head-to-Head contests (H2Hs), and both of these Cash Games have similar methodologies and strategies. Today, we’ll take a look at H2Hs, specifically, what they are, what to look for when playing them, and some strategy advice to employ.

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What are They?

Cash Games (50/50s, H2Hs) are contests in which the entrant typically doubles his money by finishing in the top 50 percent of entries. These games differ from GPPs (tournaments), where entrants are paid based on finish in a tiered fashion (first place wins the largest prize, second place wins a smaller prize, and so on), and less than 50 percent of entrants win. Head-to-Head (H2H) contests are contests in which you play against only one opponent, and the winner takes all. H2Hs are a type of Cash Game because half of the field wins and doubles its money, though there are elements of a tournament involved here too. You’re rewarded for finishing at the top of the standings, you have to beat the entire field to win, and there are certainly opportunities to take risks.


The general strategy to follow for H2H contests is similar to 50/50s, with a few differences.

  • Take a safe, risky approach. This may sound counterintuitive, but it makes sense for these contests. In Cash Games, the general strategy is to set your lineups with enough built-in safety (high-floor, low-risk options) that you finish among the top half of entrants and cash. In H2H contests, it’s you and one other entrant, mano a mano, so you’ll need to take a little more risk than 50/50s with larger fields. You should absorb the amount of risk located somewhere between 50/50s and GPPs.
  • Remember that you automatically have a 50 percent chance to win, so there is certainly room for a little bit of risk taking in your entries, as mentioned above.
  • Play multiple H2H contests each night, if you’re entering public contests. Your odds are solid at 50 percent, so remember that for all of the losses you suffer, you’re equally as likely to win. The return on investment (ROI) is high.
  • Don’t be quick to fade chalk. The “chalk” plays of the slate are those that are the most popular and will be included in many entries. It’s easier to pivot from chalk plays in GPP contests, but in H2H contests, make sure to stay competitive by paying attention to chalk plays
  • If playing against a friend, tailor your approach based on your friend’s skill level and tendencies. If the friend is a risk-taker, play it a little safer. Riskier plays can pay off big, or they can go the opposite direction, so playing it safe gives you a nice in-between position. If the friend typically plays it safe or goes with the chalkiest plays of the night, mirror that approach to a point, but make a couple of riskier plays to separate from your opponent.
  • High-floor plays are always the way to go. Don’t target boom-or-bust options. Instead, target moderately high-floor, higher-ceiling players who provide a little more upside with a little less security.

What to Look For

H2H contests pop up frequently on DFS sites. They can be set up by anyone and played by anyone. The simple method of creation, the ability to control the game, and a 50 percent chance of winning make these games popular.

Skill Level
If you’re looking to join a H2H, pay attention to the opponent. No matter your skill level, you don’t want to find yourself facing an experienced pro. This is especially true if you’re a beginner. Scope out potential opponents, and do some digging into their skill level and record. A cursory glance at a player’s username or profile is all it takes to gauge skill level. On FanDuel, an icon will appear next to username, and clicking that icon will tell you if a few stats, such as number of contests played (500+ or 1,000+) and if they’ve won a large amount of money over a certain number of games. On DraftKings, badges are awarded based on XP (experience points earned from playing contests), so you can compare badges to look for a matchup that should be fairly equal.

Creating Your Own Contest
Instead of joining a H2H, why not create one? These contests can be public or private, so this really goes back to skill level. If you’re confident in your H2H abilities, create a public contest, but if you have a little more trepidation, create a private contest. In private contests, you choose who you invite to be your opponent, and this can be users you’re familiar with on your site of choice or (most often) friends.

Playing against friends is the perfect way to hit a H2H contest while knowing your opponent’s skill level. When playing against friends, it’s recommended to make the stakes low. After all, you want to maintain a relationship with your opponent after the scores are finalized. It’s nice to win a few bucks off of your buddy, but don’t get personal, and don’t get carried away. Have fun against your friends, and if you can build your bankroll a little bit, that’s just a bonus.

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Whether you’re new to daily fantasy basketball or a seasoned professional, be sure to check out our Daily Fantasy Basketball Glossary. You can get started with Why “Points Per Minute” is the Single Most Important Stat in DFS or head to more advanced strategy — like The Do’s and Don’ts of Building a Contrarian DFS Lineup — to learn more.

Zachary Hanshew is a featured writer at FantasyPros. For more from Zachary, check out his archive and follow him @zakthemonster.

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