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I have a confession to make. When I write or talk fantasy baseball I am referring to head-to-head (H2H) leagues most of the time, primarily 10-12 team dynasty leagues (AL/NL) – for now. That’s been my experience for well over a decade. 

My fantasy baseball journey is expanding to several different types of leagues this year. I joined my first NFBC league. I am also part of three separate roto leagues, (12 teams – all on Fantrax) and a Draft and Hold league (also on Fantrax). Heck, I’m even co-managing a team in a 16 member startup dynasty league (points, Yahoo). 

2022 is going to be a wild ride! 

Now that I got that out of the way let’s get to straight to business and give you some H2H strategies. 

Let’s Define a H2H league: 

Typically, matchups are defined by Wins, Losses with the possibility of a tie on any category (W/L/T).  You face a different opponent each week with daily or weekly lineup settings.

To win a match your team has to outscore your opponent in every category (without a tie). 

H2H categories 

Depending on your league format – this can be either 5×5 or in some cases, 6×6. 

I’ll stick with 5×5 as the standard, for the sake of keeping things simple. 5×5 categories usually looks something like this:

R / HR / RBI / SB / AVG  for hitters, W / K / SV / ERA / WHIP for pitchers. 

What makes H2H fun?

Some love H2H and some absolutely hate it. 

Why do I like it? Who cares, it’s fun! I love the unpredictable nature of the format. You aren’t given an opportunity to become lazy at any point during the long season. 

You always have to be ready to strategize from the get-go. Every team is different and knowing who you’re up against will matter on a weekly basis. If you want a shot at a few weeks of meaningful fantasy baseball games in September, look no further. 

I’m looking at you, Wilpon. 

Sizing up your opponent

Exploit the strengths and weaknesses.

In some cases, there will be an owner(s) who simply won’t pay for saves or stolen bases. I, for one, am guilty of not paying for saves. Now, it’s not that I don’t value the stat – I just think closers (outside of the elites) have short-shelf lives in today’s game.

Getting back to the point – if your team happens to be strong at SBs and SVs then you already have a leg up on those two categories.

Weak spots can be many things. Injuries to superstar players or players in prolonged slumps.

If your team is on the receiving end of these tragic circumstances, this is where a deep bench would benefit you. If that is not an option then seek out the wire for favorable matchups.

ABS – Always Be Streaming

There are plenty of streaming options available, like Netflix, Disney, Hulu, but we’re not talking about anything you can watch. In fact, if you’re reading this – YOU ALREADY KNOW. 

If injuries have decimated your roster – Make up your losses by streaming. If you stream pitching, do the research on the matchups for the week. You don’t want to obliterate your ratios – pitching blowups are the hardest to come back from. I can’t tell you how many times I streamed a starting pitcher who imploded in the most glorious manner. The torture scenes in Saw movies don’t even compare to how mangled my pitching numbers looked some weeks.   

Which leads me to:

Explore the weeks matchups


Prepare in advance. Take a look at your pitching corps – the starters in particular. What teams will they be facing during the week leading into next? Your aces aren’t the ones to worry about. It’s the other guys rounding out your staff. Will they be pitching in a favorable park? Or will they be slated to hit the bump at Coors field? 

If your week starts off horribly due to an implosion on the mound know this: all is not lost. Your ERA and WHIP are most likely toast, but you can still salvage your week by streaming the wire to go all-in for K’s and if your lucky – Wins. 

On the flip side – If your pitching opens the week in a glorious manner, then carefully map out who you will start or bench in order to maintain your numbers. 

Keep in mind that starting pitchers aren’t the only pitchers to stream! A savvy owner who is light on closers can keep a close eye on major league teams who have utilized their closer on back-to-back nights – this is something I have done for years (although not always successfully).  In order to do this right, you would have to pay attention to the direction some managers take when resting their closers. It doesn’t always work, but when it does it’s awesome. 

In case you didn’t know – Fangraphs has a roster resource section that is extremely useful. Closer depth chart is one of them. 


I’ve come to enjoy streaming hitters more and more than I do pitching (sorry Michael!). I’ll still dive for some pitching streams from time to time, but hitters have become my go-to now. 

The best way to approach hitting streams is to look at player handedness. Platoon players get a ton of looks on my squads on a weekly basis. Lefty on the mound? I’m calling on the lefty masher right off the wire.

Got a friendly matchup against a vulnerable pitcher in a hitter-friendly park? I’m also looking to stack hitters from the same team to pile on the counting stats. 

You have some guys on teams with off days (usually on Thursday)? Make sure to snag a player or two for that one-day rental. 


Don’t pay attention to lifetime HvP stats. I mean that. It’s a wonky stat and almost unreal how some players own one another, but it has no place in Fantasy baseball. 

H2H leagues have an air of unpredictability surrounding them. On any given week someone with a fairly mediocre team can either wipe the floor, squeak out a win or break even with a tie. It can be a very frustrating outcome, but with the right strategic play, you can find ways to stay on top. 

These are strategies I have used over the years with consistency; however, it doesn’t always guarantee success. Like with stocks, always use caution before making a decision – research and stay ahead of the pack by digging deeper than anyone in your league. 

Thanks for reading!


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