Winning Fantasy Baseball Strategies — Weekly Head-to-Head Points Leagues

Chris Parsons
6 min readMay 22, 2024

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Part I: Starting Pitching

After I wrote my first article about my initial fantasy baseball strategy hypotheses, which can be found here, I ended up joining a second fantasy baseball league so that I would have more opportunities to test my strategies.

Advanced pitching statistics

I ended up joining a 10 team, weekly head-to-head points league that has been active for a few years that had a manager leave the league before the draft. The additional league that I joined has many of the same settings as my first public league that I joined and discussed in my first article, but some of the key differences are as follows:

· The second league has 5 starting pitcher spots and 3 relief pitcher spots in the starting lineup (rather than having 7 pitcher starting lineup spots that can be any combination of starting pitchers and relivers in my first league). This is very important, and a key component of one of the strategies that I will discuss.

· Extra base hits are 2.5 points, on top of the total bases recorded on an extra base hit. There are not any added points for extra base hits in my first league. As an aside, I think that the 2.5 additional points for an extra base hit is a great scoring setting, as it attempts to get the point value of hitters closer to the point value of starting pitchers. In my first league that does not have this scoring setting, the points earned by starting pitchers are greater than the fantasy points earned by hitters.

· 6 teams out of 10 make the playoffs, with the top 2 teams earning a first-round bye, and there are no divisions (compared to the top two teams in each of the two divisions making the playoffs in my first league). As another aside, I think divisions in fantasy sports are pointless and can create vast inequities between divisions. Since the divisions in a fantasy league are completely arbitrary, one division can end up with much stronger teams than another division, and a team with a worse record in an easier division could make the playoffs over a team with a better record in a harder division.

Generally speaking, the two leagues have very similar settings, but the strategy takeaways that I will discuss here will all be geared towards my more competitive second league that I joined. The second league that I joined is full of active managers and has a higher level of competition than my first league, so it’s a much better testing ground to assess my managerial skills and my gameplay strategies.

After 8 weeks of the baseball season, we are at about the 40% mark of the fantasy baseball regular season schedule. At this point, I am 8–0 in my first league and have scored the most points in the league, and I am 5–3 in my second league (second best record in the league) and have scored the most points in the league. In my second league, my goal for the regular season is to finish in the top 2 of the standings and secure one of the two first round byes in the playoffs.

So far, I believe that the three most important managerial aspects of weekly head to head points fantasy baseball are maximizing volume (at-bats and innings pitched) every day in your daily lineups, constantly evaluating your stable of starting pitchers on your roster and on waivers to aim to start the 11 best starting pitchers that you can in each weekly matchup, and overall roster construction. I believe that these are the three most important aspects to focus on that make the most meaningful impact on winning or losing.

I will do a deep dive into each of these strategy principles. This article in Part 1 will focus on managing your pitching starts.

Managing Pitching Starts

Your top managerial priority each week should be evaluating your current roster and the starting pitchers available on waivers to determine the best possible combination of 11 (or whatever your league’s max is) pitching starts that you will use in each matchup week. Given the high points ceilings that starting pitchers have, you should reach the maximum number of pitching starts that you are allowed to start each week.

Tyler Glasnow

At the beginning of each matchup week, look at the starting pitchers that you have on your roster, and see how many starts you will be able to get from them in the matchup week. If I am using a valuable roster spot on a starting pitcher, I am most likely going to start them anytime they are starting, unless the matchup is clearly very unfavorable for them and there is a significant risk of them earning negative points from the start, or if there are many better pitchers available on waivers for the week.

Once you identify how many starts you will get from the starting pitchers on your roster that week, identify how many starts from pitchers on waivers you will need to acquire for the week. For example, if the pitcher start maximum for a matchup week in your league is 11, and you identify 7 starts from the starting pitchers on your roster for the week, then you know that you need to acquire 4 pitcher starts from waivers for the week.

To identify the pitching starts that I want to acquire on waivers for a weekly matchup, I look at the schedule for the matchup week for the available pitchers. I then identify my top acquisition targets based on the following criteria:

· The projected points for a pitcher in each start.

· The quality of the offense that they would be pitching against.

· Pitchers that pitch for a good team, so that they have a higher chance of securing a win.

· Pitchers that are pitching in a favorable ballpark for pitchers that day.

· Pitchers that have a strong ratio of strikeouts-to-walks.

· Pitchers that have a track record of pitching deep into games so that you increase your chances of securing a Quality Start (pitching 6 or more innings and giving up 3 or less earned runs).

Then once I identify the pitchers that I want to acquire to start that week, I formulate my plan for when I will claim them off waivers. If I believe that the pitcher is highly desirable and that they may be picked up by another team, I will pick them up a few days before their start. But if I think I might be the only team looking to acquire them, then I will wait until the day before their start to pick them up, which allows me to make use of that roster spot for other players during the matchup week rather than having it be taken up by that starting pitcher before their start.

Lastly, after a pitchers’ start during the matchup week that I acquired them for, I will drop them to clear the roster spot so that I can use it for other options to maximize my potential points, unless that pitcher became someone that is valuable enough to hold onto for their next start.

If you are in a tight matchup, just be cognizant of the possibility of a huge blowup outing by a starting pitcher costing you negative points. If I have a lead, I will be careful to assess all of my starting pitcher matchups remaining for the matchup week, and I will consider not starting a pitcher if I feel like they have a higher likelihood of surrendering a large amount of earned runs and earning a loss, thus yielding negative points.

Lastly, it’s important to check each day that you will still reach the max pitching start limit each week, as starting pitcher rotations can change during the week based on injuries, matchups, extra rest, or rain outs. For example, a pitcher on your roster that was expected to start on the last day of the matchup week could get their start pushed out a day into the next matchup week due to a rainout, and then you would need to acquire another start to make up for that lost start and the corresponding lost opportunity for points.

Check back here soon for my deep dive into the next strategy to deploy in winning your weekly head to head points fantasy baseball leagues — maximizing volume in daily lineups!

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