Two years ago, I sneaked into a league’s playoffs with a hodge podge of pitchers no one had ever heard of and ran up against the commissioner in the first round. We ended our matchup tied in categories at 5-5. At the time, the Yahoo tiebreaker was the head-to-head record during the season.

Well, I’d had an oddball year and somehow had absolutely dominated my regular season matchups against the commissioner, so I moved on to the next round. He took it so well that he fired off a couple of “What is this injustice?!?” emails and then changed the tiebreaker the next season to whoever had the better regular season record.

This random chaos is the absolute beauty of playing H2H Categories in fantasy baseball.

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H2H Categories League Overview & Strategy

*Of note: There can be as many categories as people want to throw in a league, but for the purposes of this article, we’ll stick with 10 total for ease of discussion.*

Know the Setup

Fantasy baseball has an infinite number of options to use in a league at this point. I’m currently in a dozen H2H leagues, and no two are alike. Therefore, you have to know the setup in your league in order to develop a strategy.

One of the primary things to know is whether each H2H matchup is scored as one game or 10 games. For example: If you win six cats, and your opponent wins four, is your overall score tallied as 1-0 (for winning the matchup overall) or 6-4 (a W/L assigned to each category)? While scoring it as one game is much closer to the spirit of traditional roto leagues, many people enjoy the feeling of getting “wins” each week, even if they don’t get the majority.

You also need to know how waivers, free agents, and trades are handled. Even though you’re going to draft perfectly, what other moves can you make if you need to? Does your league have daily waivers, or will you be very busy on Sunday nights trying to do pickups and drops? Can you make lineup changes during the week? These are all questions you should ask prior to your draft.

Know the Categories

While this is the definition of obvious, you have to know what categories are in play in your league before you can come up with any sort of strategy. A lot of leagues are still traditional 5×5 (R, HR, RBI, SB, AVG | W, SV, K, ERA, WHIP), and this will be the default of most mock drafts. But baseball has so many options that you need to be sure you’re in a league that counts strikeouts (K) as opposed to K/9, K/BB, K%, etc. It can get quickly quirky, and you can draft entirely wrong if you don’t pay attention.

Also, pay attention to any minimum/maximum numbers involved. Some leagues will have a minimum number of innings pitched per matchup or a maximum of innings pitched per season. A strategy of nothing but relief pitchers probably won’t work if you have to get 40 innings pitched in seven days. These are the types of little things that make a huge difference when setting up your draft plan. Which leads me to another point…

Have a Draft Plan

Coming up with a draft plan is one of the most fun parts of any fantasy baseball season. Excelling in every category is practically impossible, so you need to decide which categories you’re going to target and when. This is where using a Mock Draft Simulator becomes your bread and butter for the days/weeks/months leading up to your draft. Getting a feel for the players you’re interested in or where you can find hidden gems for some categories is the best way to know which direction to go when the time crunch is on.

Are you going to ignore a category entirely? You should decide this before you start so that you can stick to it throughout the draft. Some managers prefer to draft in a “best player available” mode, but this is trickier to do in an H2H categories league since you’re looking for specific strengths, not just points.

You also want to keep an eye on how others are utilizing their draft plans. For example, if someone drafts three relief pitchers in a row, you probably don’t want to try to get in an arms race with them. Instead, target what they’re not so you can possibly make trades later.

If you win six out of 10 categories every week, chances are pretty good you’ll make the playoffs and do some damage. That may seem obvious, but all too often, fantasy managers end up with a perfectly balanced lineup that is destined to go 5-5 a lot. Just think of it as trying to win “the series” every week.

And don’t be afraid to get bold and wonky. One of my favorite seasons was when I went extremely pitching-heavy and drafted as many leadoff/top-of-the-order hitters as I could. It certainly shuffled a lot of things around on draft day, and it can be fun to be the contrarian at the table.

Embrace the Randomness

At some point during the season, you will run into a juggernaut of a performance that just buries you in a head-to-head matchup. Your opponent will hit 19 HR with 80 RBI, and 20 SB, and destroy every pitching category. The stars will align, and you will find yourself on the losing end of a 9-1 week. The next week, your opponent will have their starting pitching studs get lit up and hit four total HR, and you’ll have an average week that secures a 9-1 win.

Roto purists will tell you that a baseball season is too long, too intricate, and too complex to be decided by <scoff> randomness </end scoff> of this nature. This is true, and don’t get me wrong. A regular rotisserie league has many benefits and strategies unto itself.

But the randomness is the point of H2H. What you want to do in a draft is try to account for what “should” happen while wholly embracing the fact that “random gonna happen,” and there’s no point in hating it.

Draft well enough to cause your commissioner to change the rule settings. And, as always, good luck!

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