MLB DFS Strategy: Contest Selection and Single Entry Success

Mark Kieffer gives some tips on how to be a successful and profitable MLB DFS player in the second part of his MLB strategy series.

This is the next installment of my MLB DFS Strategy Series. If you missed the first one about Bankroll Management and Contest Selection you can check it out here.

Hello, RotoBallers, and thanks for taking the time to read this MLB DFS strategy piece! If you're here, it's likely because you want to be a better DFS player and learn more about how to be a sustainable DFS player who doesn't have to deposit more money in their account every week.

When I was writing my previous article and discussed contest selection, I realized there is so much more to it that I did not get a chance to touch on that has helped me go from being a losing player to a profitable player. So I wanted to share more with you here about how to choose the best contests with the goal of helping you win more often and deposit less often.

The Background

Why am I talking about this as opposed to talking straight-up lineups, though?

I truly believe the reason why I am a profitable MLB DFS player is due to bankroll management and contest selection more than setting good lineups. Yes, there is a skill with creating lineups, but MLB is such a high variance sport when anything really can happen in a given night. If you follow sound principles and strategies to spend your money and enter contests, you can limit your losses while biding your time for that winning night. A suboptimal lineup can go off in MLB and they often do.

Previously, I walked through some math on how to determine bankroll and how much to wager in a given night. I am primarily a tournament player, meaning I do not enter cash games, and I advocate for someone that follows my route to stick to a 2% of bankroll budget on a given slate.

Even if you are interested in cash games, until you know your skill level is good (track record of a win rate of above 55%), I would not wager the 10% recommendations that most give. In my opinion, that 10% of bankroll in a given slate is geared towards someone that is a skilled player. If you are unskilled and wagering 10% of your bankroll in cash games, you could quite easily be out of your bankroll in a couple of weeks.

Enough of the re-hash, let's get to the new part:

Contest Selection - A Deeper Dive

Let's say you have a bankroll of $1,000. I would suggest if you were to play exclusively tournaments, to play no more than $20 on a given slate as 2% of $1,000 is $20.

If someone gave me that advice a couple of years ago, I would have said "oh okay cool" and then entered 1 lineup into a single $20 tournament. I used to be that guy. I was like "why should I play all these contests when I can just stick it in one contest?" The same idea holds true for cash games in that I might have entered one $20 Head to Head or one $20 50/50 contest as opposed to twenty $1 cash games.

This is not a good example of efficient contest selection.

I can speak from experience here, but the lower the buy-in for a contest there is, the less sharp the entrants are on average. On average, the pay line for a $1 contest is lower than the pay line for a $10 contest. There are always exceptions to this for a slew of reasons, however over the course of 180 slates, you will find on average this to be true. Pay lines are the points needed to cash in a contest, for tournaments usually between 20% and 26% of the field depending on the contest.

I did an experiment a couple of seasons ago where I entered a $1, $3, $5, $12, $25, $50, and $100 on a given slate over a large chunk of the season.  I will attest that the $100 contest on average had a higher point total to make the pay line than the $1 contest.

For MLB, I prefer the single entry contests. If I am playing about $20 in an evening, I typically play a $3, $5, and $12 single entry contest on that slate. I would rather spread my entries across multiple contests than put all of my eggs in one basket.

If you entered a single lineup in each of a $3, $5, and $12, and say it's about a 72nd percentile lineup it's right on the bubble between cashing and not. You might not cash in the $12 but you could cash in a $5, $3, or $1. I have had it happen before many times.

It can still sting to be down for the night, but you might be down something like $8 or $14 rather than the entire $20. On a bad night, if you can not go to $0, it's a small win in my opinion. When you are like me and playing tournaments, you are bound to have bad nights and cold streaks.

If you take this idea for cash games, it is applied the same way. If I had $20 to spend on cash games, I would rather enter twenty $1 50/50s than a singular one. Or if I wanted to play head to head -> same idea. If you are a skilled cash game player and you spread out across contests, unless your lineup is just horrid, it's difficult to lose all $20. I am not a skilled cash game player, so I frequently lost all $20. Long story short: don't hit me up on Twitter asking me for cash game advice.

Single Entry Tournament Strategy - The Next Level

Going back to tournaments, if you do play a style similar to mine where you enter the single entry contests, I am going to share with you a couple of pointers that were passed onto me at one point. Shout out to the person that told me this, they know who they are!

If entering multiple single entry tournaments (such as my $3, $5, and $12 example), instead of entering the same lineup 3 times, I enter 3 different lineups. What this does is gives me 3 chances to take down a tournament.

Now, what I will say is that doing this strategy can be a little tilting at times. For example, the other night my $3 lineup finished 46th in a 2,000 entry tournament, which was good enough to 3x my money ($9). My other lineups in the $5 and the $12 did not cash. I lost $11 on the slate. Had I entered my $3 into the $12, I would have won around $35 in that contest. For some, that can be frustrating. But when I do that, what I remind myself is that my favorite lineup was in my $12, so I likely would have entered $20 and taken back nothing, losing $20 on the slate. Losing $11 instead of $20 sounds a lot better.

I just know for MLB, it's hard to pick the correct stack to go off, so if I choose 3 stacks I really like I give myself 3 chances to win a tournament that slate. In a Single Entry Tournament, I never go completely off the wall or anything. I will typically put my chalkier lineup in my lowest dollar tournament and my less chalky lineup in the higher dollar tournament (the beauty of the Single Entry is my "less chalky" tournament is usually the projected 5th best stack of the night out of the 24-30 teams playing during that slate).

I don't have any science behind this, but I find that because the lower dollar games are less sharp. Less sharp means it's easier to cash with a chalkier lineup.  At the higher dollar mark, the players are sharper and more risk-averse as well. In a recent $12 entry, I played what was easily the 2nd best stack of the night, and it came in under 5% owned. I didn't win, but I loved the position I was in if the stack were to have come through.

A lot of these decisions are going to have to deal with your mindset and demeanor. You know yourself best, play the way you like. If you enter Single Entry Tournaments and want to enter 1 lineup across 3 contests or 5 contests, then go ahead and do it that way.

What I want to reiterate is if you spread out your entries instead of consolidating them into one entry, you will play in less sharp contests and give yourself more ways to cash if you are on an off night.

The other thing I should mention is ego. When I first started playing DFS, I wanted to enter the $25 or the $50 contests. Heck, I wanted to be in the $5,000 contests. I wanted to play high-dollar contests, not just to win large prizes but to hang with the sharp players. I believed that in order to be a good DFS player, it was all based on how large of stakes you played.

Let me tell you: that mindset is a great way to go broke quickly.

It is easy for me to say now because I have played in some of those contests, however, I have no shame in picking up a bunch of $1, $3, $5, contests instead of playing in big ones. My profitability is higher in the lower dollar contests and my goal is to earn a profit each MLB season. Profit means I get to keep playing. I'm trying to be like NBA Youngboy: Never Broke Again.

There is no shame in playing in $1, or $3, or $5 contests. The only downside is those fields are larger than the $100 contests. The lower dollar contests are easier to cash generally but harder to win than the higher dollar contests.

Final Thoughts

Playing in multiple, lower dollar contests rather than 1 higher dollar contest is the way to give yourself better chances to win, and less of a chance to go to $0 on a given slate. Higher stakes contests are tougher to cash, the players are sharper than the lower stakes contests.

Playing multiple Single Entry Tournaments with a different lineup in each contest is a way to increase your chances of winning a tournament that night, as long as you can mentally handle the swings of it. I personally play tournaments to win, so I take this approach.

Make sure you check back next week as I continue this series of DFS strategy articles that I will be doing here at RotoBaller! Good luck and play smart!