For a long time, I treated all of my fantasy baseball leagues like they were the same. I played in a keeper league and made the playoffs every year, winning multiple times, and that made me think I had fantasy baseball pretty much figured out. I was young and dumb back then and at least one of those things has changed. I have come to realize that not all fantasy baseball formats are the same and you are doing yourself a major disservice if you fail to take the format into account both while preparing for the draft as well as during the season. It is with that in mind that we take a look now at one of the most common formats: head-to-head leagues.

As Michael Stein touched on in his draft guide article Starting a Fantasy Baseball League, one of the most important decisions in creating a fantasy baseball league is whether to play in a head-to-head or rotisserie league. This is also a crucial part of determining what league or leagues to join. While both formats can be a lot of fun, they are not all things to all people. After we help you determine if head-to-head leagues are right for you, we will look at some of the key considerations for winning those leagues.

Why should you choose a head-to-head league?

   1.   You want to be engaged every week.

This is probably the best reason for joining a head-to-head league. In a head-to-head league, you face a different opponent every week. That means you potentially get to sweat out a result every weekend. Not every matchup with be close, obviously, but you have over 20 opportunities to have an exciting finish. In leagues with daily transactions, you get the added excitement of making roster moves and lineup decisions over the weekend to try to put yourself over the top or ensure you stay ahead. That kind of excitement simply does not exist in roto leagues.

If you think you may have trouble staying engaged in a rotisserie league where the standings may not change significantly for weeks at a time, head-to-head leagues provide a nice contrast. Many smart fantasy baseball players will enter at least one head-to-head league even if all of their other leagues are rotisserie. The week-to-week excitement of the head-to-head league ensures the player will stay engaged with fantasy baseball and pay attention to all of their leagues when they might not have otherwise. It is easy to forget the baseball season is almost two months longer than the NFL season, and one way to make it go faster is to have a different matchup to focus on each week.

   2.   You have playoff fever.

The other big advantage head-to-head leagues have over roto leagues is the playoffs. In roto leagues, the fantasy team with the most roto points on the last day of the MLB regular season wins. You may get some prize money for finishing second or third, but you don’t get a shot at the fantasy championship.

Head-to-head leagues almost always culminate in a playoff. The goal in those leagues should be to simply make the playoffs. Once you get there, anything can happen. Playoffs can add weeks of excitement that wouldn’t otherwise exist. You get the playoff race itself, where teams fight to make the playoffs, followed by each individual playoff matchup. Roto leagues can be exciting themselves, especially in the last couple of weeks, but often only for the top two or three teams.

   3.   You like talking trash/making side bets.

We have all played fantasy with people who live to make side bets or talk trash or maybe just beat their arch nemesis. All of those are possible in rotisserie leagues, but head-to-head leagues provide you more opportunities. You will typically get to play each player at least once in a head-to-head league, which means 20-plus opportunities to make a bet on the outcome of a given matchup. Even if you don’t make a bet, each matchup is an opportunity to earn bragging rights.

Four years ago, my friend streamed Chad Bettis in Coors Field on a Sunday to win our matchup in the last week of the regular season and knock me out of the playoffs. I still hear about it to this day, and just the name Chad Bettis is enough to raise the hairs on the back of my neck. Those kinds of stories are rare in roto leagues.

   4.   You are experienced in fantasy football or head-to-head in other sports.

A lot of fantasy players get their first taste of season-long fantasy by playing fantasy football. If that is the case and you want a baseball experience similar to what you are used to, start with a head-to-head league. Rotisserie leagues can be a ton of fun in their own right, and in some ways they involve even more strategy, but first-time fantasy baseball players are often better off in head-to-head leagues.

   5.   You are looking for a new challenge.

Conversely, if you are already familiar with roto leagues, head-to-head leagues offer a unique challenge. We discuss the differences in much greater detail below in the section about head-to-head strategy, but they can be fun for fantasy players who are used to roto leagues.

   6.   You don’t mind luck playing a larger role.

Again, fantasy football players already know how important luck is for winning. In any head-to-head format, regardless of the sport, it is possible to have a good team but still miss the playoffs as a result of facing hot teams week after week. For beginners, this could actually be a good reason to play in a head-to-head league, since you don’t necessarily need a good team to win a bunch of matchups. At the very least, you should be okay with knowing luck will play an even larger role in head-to-head leagues than in roto leagues.

   7.   You like punting categories.

We will look at this in far more detail in the strategies section, but it is important to consider when choosing a league format. If you usually employ a punting strategy, or you want to try it for the first time, head-to-head leagues are generally your best bet.

How do you win a head-to-head league?

   1.   Be Aggressive, B-E Aggressive.

Joe Gallina has a great article in our draft guide on the importance of patience for fantasy baseball. Even if you have already read it, you should go read it again, because being patient is that important. That being said, the nature of head-to-head leagues is such that you simply cannot afford to be as patient as you would in a rotisserie league.

In a rotisserie league, all that matters is where you finish in the standings at the end of the season. If you have a terrible first half and an amazing second half, the stats all count the same. It is not uncommon for a fantasy team to be at or near the bottom of the roto standings for the first two or three months but turn their season around with a strong second half. That simply isn’t possible in a head-to-head league, especially a points league.

Points leagues award a win, loss, or tie at the end of each week based on which team has scored the most points. Similarly, some categories leagues award wins and losses in the same way, while other head-to-head category leagues award a “win” for each category for the week.

For instance, let’s say my team is facing Howard in Week 1 in a 10-category league, and I win six of the categories. In some leagues, my record after the first week would be 1-0. In others, it would be 6-4. Knowing how your head-to-head league awards wins is extremely important, especially when it comes to being aggressive.  

If your fantasy team is 0-4 a month into the season, you probably have to take some drastic action, whether that means pursuing trades or dropping players you expected to count on coming into the season. However, that same 0-4 team could be 14-26 through four weeks in a different format, and that team can probably afford to be a bit more patient.

In either case, you will probably have to be more aggressive than you would in a roto league. That doesn’t mean dropping José Ramírez or Jack Flaherty if they get off to a slow start, but it could mean looking to add some steals if you are losing that category every week.

Another way in which you should probably be more aggressive is in dealing with injuries. It is easier to wait for Trea Turner to come off the disabled list in a rotisserie league, where you can make up ground late and may even have a games played limit. You might not have that luxury in a head-to-head league where you could be 0-5 by the time he comes back. Especially in leagues with shallow benches, spending more than one or two roster spots on an injured player can be an anchor on your team’s season.

   2.   Ride the hot pony like you are Ginuwine.

On the face of it, this advice should be obvious. Any time you can live your life like Ginuwine that is probably the way to go. Or, perhaps more accurately, when every week matters in the standings, you will probably have to chase some fringe players who are riding a hot streak.

Even if it should be obvious, it is crazy how many fantasy players roll out the same lineups in head-to-head leagues week after week, regardless of how their players are doing. Again, you shouldn’t drop good players just because they are slumping, but especially in leagues with deep benches and/or IR slots, there are almost certainly opportunities to get some juice from the orange, to mix metaphors, while a player is hot.

   3.   Stream pitchers, especially towards the end of the week.

Again, this is an area that often gets neglected by fantasy players while the season goes along. You never want to drop a good player just to chase a win for one week, but sometimes you have to risk losing a marginal player to try to chase in a category or categories where you trail. Picking up a few starting pitchers in favorable matchups throughout the course of the season could be the difference between winning a fantasy championship and missing the playoffs altogether.

   4.   Aim for balance.

Unless you punting a category or categories (more on that later), the best strategy is to try to form a team that will be above-average across the board. Sure, winning the home run category every week is nice, but if you are beating your opponent in home runs by double digits every week, that production is essentially going to waste. There is more of an advantage to hitting the most home runs in a roto league compared to a head-to-head league. In a head-to-head league, you should be far more willing to deal from a position of strength to shore up your weak spots.

   5.   Bring on the punt team.

Punting can be a viable strategy in any league that uses categories, but it is a better strategy for head-to-head leagues, especially ones that award one win or loss per matchup. In head-to-head leagues, your goal shouldn’t be to have the best team in the regular season. Your goal should be to make the postseason. While it would be nice to win every matchup 10-0, that isn’t necessary for making the playoffs. You could conceivably win every matchup 7-3 and still comfortably make the playoffs. That makes punting one or even more categories a viable strategy. That is one of the reasons a lot of head-to-head leagues have start minimums for pitchers, so that you cannot punt wins and strikeouts and focus solely on ERA, WHIP and saves. Without start or innings miniums, that is a viable way to win a head-to-head league that you probably couldn’t get away with in a roto league.

The other reason to punt in head-to-head leagues is you can win some categories in any given week even if you are “punting” them. The best example is batting average. You can get a head start on winning the counting stats by punting batting average (or on base percentage) during your draft. That being said, even a .240 hitter will have weeks when he goes 7-for-15. Just because you punt batting average doesn’t mean you will lose it every week, whereas punting batting average in a roto league means you will (probably) only score one or two points in the category.

“Let me Explain. There is no time. Let me sum up.”

Head-to-head leagues are a staple of fantasy baseball, and for good reason. They can bring a lot of excitement throughout the season while offering opportunities for different strategies than roto leagues. While they are not for everyone, they could be for you, and if you have made it this far into our head-to-head league article, you should probably give them a shot. At the very least, you should now be equipped to handle everything a head-to-head league can throw at you.