👉 TAP TO SAVE 50% WITH CODE SPRING
X
Lost password?

Don't have an account?
Gain Access Now

X

Receive free daily analysis

NFL
NBA
NHL
NASCAR
CFB
MLB
MMA
PGA
ESPORTS
BETTING

Already have an account? Log In

X

Forgot Password


POPULAR FANTASY TOOLS

#1 Expert Projections
Save 50% Now
Import Your Leagues
Props Tool
Compare Any Players
Compare Any Players
24x7 News and Alerts

All-Star Break Rest-of-Season Strategy: Head-to-Head Leagues

Happy All-Star Break to all you fantasy baseball nerds out there. As we sit through what seems like the longest four days of the summer, I thought it might be helpful to discuss some general season-long strategy for the rest of the year. Of course, strategy can differ greatly based on your league type, so I'll be supplying some thoughts for both rotisserie and head-to-head leagues.

In head-to-head leagues, the goal is to find a way into the playoffs while also preparing for them. I'm going to assume we are working with a weekly matchup, redraft format in which points are accrued weekly, walks and HBPs help batters, and strikeouts hinder them. At the end of the week, you get a win, loss, or tie for that week, and a certain number of teams make the playoffs. This format is much like the majority of fantasy football formats. With that in mind, it's much more likely that a middle-of-the road team  can find it's way to the championship than in a roto league (which I've discussed in depth in a previous article). Likewise, it's very possible that the best team in the regular season can lose in the first week of the playoffs. While this nerve-racking amount of parody and varience disturbs me, there are plenty of fantasy baseball players who enjoy it.

So, let's look at three different, general scenarios that you may be in right now in your head-to-head league and talk about how you might effectively go about making the playoffs and continuing your success through to the championship matchup. If you have specific questions or you want to chat more strategy, I'm always open. You can find me on Twitter @BellRoto. Best of luck to you in the home stretch!

Featured Promo: Save 50% the regular price with discount code SPRING, for a limited time. Exclusive access to our Team Sync platform, DFS cheat sheets, Lineup Optimizers, betting/prop picks, and exclusive content from Nick Mariano and Eric Cross! GAIN ACCESS NOW

 

H2H League Strategy Rest-Of-Season

Top 33% - Two Games or Less Out of First Place

The variations of head-to-head leagues that exist make specifics very difficult in this type of article, but there are a few main foundations that need to be taken into account at this point in the year if you'd like to have success in these next few months. First, the playoffs allow for more owners to be in the running for money and the championship. Thus, as long as owners don't give up on their teams, there should be more competition for a longer period of time than in roto leagues. Second, the fact that the playoffs exist means there is a shorter regular season. This means that h2h leagues are likely close to 65% or 70% over by now instead of roto's 55% or so. Lastly, the fact that you're matching up against one player each week provides variance in that you could both go on a huge run, winning five or six weeks in a row against poor opponents, or go on a cold streak, playing the top point-scorer three times in a row and losing mulitple weeks despite your team performing well compared to the league as a whole.

This is why I no longer play head-to-head fantasy baseball, and it's also why I would jump at the chance to play in a sensible roto-type fantasy football league. Even still, there is plenty of strategy that goes into h2h leagues, allowing for us to analyze such strategy for the rest of the year.

Let's assume, for simplicity's sake, that you're in a 12-team head-to-head points league (no divisions) that has six playoff spots. This category, then, would likely identify the top four teams in the league at the All-Star Break. These teams are likely going to make the playoffs by season's end, so their main concerns right now are getting as high as possible in the standings, but also preparing for the (likely) three weeks of playoffs. In this case, the top two teams would likely receive a first-round bye. That concept can also bring in a whole different bundle of strategy.

Aside from picking up high-upside waiver fodder to fill your bench, DL, and NA spots, you should also be looking to handcuff important pieces of your team if you're in this position. An example of this, similar to picking up the back-up running back in fantasy football, is stashing the set-up man for your closer. This move makes more sense in some scenarios than others (possible trade, closer struggling, set-up man really good numbers, etc.), but it should be mentioned regardless. If there is not an opportunity to handcuff one of your closers, perhaps picking up a speculative, future save-getter like Archie Bradley would be a good move.

Another non-trade piece of advice that makes sense for a team like this is fine-tuning strategy and studying opponents. Depending on the restrictions in your league, you may be able to successfully deploy a zero-RP or zero-SP approach, altering the types of players you start each week dramatically. Perhaps you're beginning to notice that speedy, stolen base threats constantly have better weeks than streaky home run hitters. Now is a good type to explore those strategies to ensure you aren't leaving points on your bench or on the waiver wire. If you can begin to guess who your first playoff game will be against, you can try to undermine their strategy as well. The list goes on in terms of mini-strategies that you can use to incrementally better your winning chances once the meaningful matchups begin.

Lastly, trading is an obvious method of improving your team, and you can amplify the waiver wire strategy above by trading risky players for predictably reliable players that better compliment the foundation of your team. You can also begin to look ahead to the playoff weeks and cater trades for those matchups specifically. This works great for starting pitchers, as you might be able to trade Jon Gray at home against the Diamondbacks for Sonny Gray at home against the Angels.

I could go on for hours on how to prepare for the playoffs, and still it might not be relevant for your specific combination of rules and regulations. My point with this section is simply that you should begin looking forward to the playoff weeks as soon as you can without hindering your chanecs at a good regular season finish. Variance and parody makes things very interesting in head-to-head points leagues that include playoffs, so preparing for those weeks when your opponents are just trying to make the playoffs can give you a slight advantage.

 

Middle 33% - Between Three and Five Games Out

It's go time, folks.

If you're in this category (likely between sixth and eighth in the specific league we outlined above), you can't afford to wait any longer for regression to come. Perhaps the player who's still barely making the playoffs can wait-and-see for another week or two. But remember that playoffs cut down the regular season tremendously, and you would rather not have to "win-or-go-home" in the final week of the season if you can avoid it.

Fantasy owners in this category should be seeking out possible consolidation trades in order to buy stud players that can help you big time on a weekly basis. You should be able to find some solid replacement value on the waive wire, and hopefully the move you made to get Manny Machado in Week 16 pays off in the first round of the playoffs in the form of five home runs and 12 RBI. Don't be afraid to be risky here, either. The owners in the section above might be looking to get rid of what we thought were slow starters because they would prefer a safer bat in the playoffs. Rougned Odor, Nick Castellanos, and Yoenis Cespedes are three relatively risky hitters that I could realistically see hitting 20 home runs between now and the time your playoffs start. If they don't, you might miss the playoffs by one game. But if they do, you might be looking at a first-round upset on your way to a big payout.

Streaming should become more prevalent for fantasy owners in this category as well, as you can no longer afford to trot out John Lackey with the hope that the Cubs score enough runs to at least get you a win. Choosing hot, lesser-known hitters with good matchups over veterans who might sit out a game can be a viable strategy to steal a few extra points as well. Whatever you can do, risky or not, to potentially steal you a win each week should be considered. You are not at the all-or-nothing stage yet, especially in the leagues that send a lot of teams to the playoffs, but you're not sitting pretty either. Buck up and make some moves if you still want a legitimate chance at winning this league.

There's not nearly as much to say about these teams because the path they should be taking is pretty clear at this point. Good luck to those of you in playoff-limbo right now, and please don't be the guy who misses the playoffs by one game because he refused to trade (or drop) the fading player on his favorite team.

 

Bottom 33% - More Than Five Games Out

While I still will promo RotoBaller's great fantasy football content that is already pouring onto our great website, there might still be time for these folks in head-to-head fantasy baseball leagues. Depending on the playoff size in your league, a nice winning streak could put you right in the thick of things. On the other hand, if you're seven games out of a playoff spot with seven games left, you can probably rip the band-aid off now and hit that "Football" tab up top.

With that being said, and this is even more important here than it was in the roto write-up, please do not completely forget about your team now that you're mathematically eliminated from playoff contention. With weekly matchups determining playoff status each week, you need to at least check-in every Sunday to make sure there aren't any injured players on your roster and that the best players on your team are starting. If you don't want to touch waivers or field trade offers, fine. But don't ruin everyone else's fun by giving the sixth place team a free win in the second-to-last week.

For those cellar dwellars that still do have a chance at a playoff spot, you better hit your league's group chat platform now and start talking some trades. Make some risks, buy some players that nobody wants, and pretend like every week is a must-win week... Because it pretty much is. I shouldn't have to tell you much more than that. The majority of fantasy advice on podcasts and in articles will be catered towards the owners in the two sections above, but you don't have to be reasonable anymore. If you think Luis Castillo and Joey Gallo could explode the next two months, go trade Jake Arrieta and Jonathan Lucroy for them. You can't afford to wait on those guys at this point. YOU NEED TO WIN NOW!

You get the gist. Rankings or buy-low/sell-high trade advice won't help you now. Go with your guy and try to make a movie-worthy miracle happen in the next handful of weeks. Good luck, soldier.

 

Conclusion

Again, hit me up on Twitter with any questions or comments you may have (@BellRoto). I love talking strategy about fantasy baseball.

For those of you looking for roto strategy advice, there should be an article posted nearby with a very similar title but a very different body. I wish you all the best of luck, except of course my fellow writers and editors here at RotoBaller with whom I share a very important set of standings.




POPULAR FANTASY TOOLS

#1 Expert Projections
Save 50% Now
Import Your Leagues
Props Tool
Compare Any Players
Compare Any Players
24x7 News and Alerts

REAL-TIME FANTASY NEWS

Juwan Johnson

Facing Reduced Role in New Orleans Following NFL Draft?
Chuba Hubbard

a Prime Bounce-Back Candidate Following Offseason Moves
Indianapolis Colts

Kenny Moore Granted his Release by Colts
Minnesota Vikings

Chad Alexander a Candidate for Vikings GM Job
Tarik Skubal

Could Return in 4-6 Weeks After Successful Elbow Surgery
Minnesota Vikings

Vikings Request to Interview RJ Gillen for GM Job
Drake Maye

Shoulder Doing "Great"
Gunnar Helm

a Clear Breakout Candidate Despite Crowded Offense?
Travis Hunter

Dynasty Managers Regret Drafting Travis Hunter?
Khalil Shakir

Offseason Addition a Threat to Khalil Shakir's Consistency?
Christian Watson

Can Christian Watson Overcome Injury History?
Pat Freiermuth

a Bounce-Back Candidate in New System
Tua Tagovailoa

Lacks Long-Term Appeal in Dynasty Leagues
Cole Ragans

Royals Hopeful That Cole Ragans Makes his Next Start
Jordan Mason

Still Holding Dynasty Value
Aaron Rodgers

Planning a Visit With Steelers
Dontayvion Wicks

What is Dontayvion Wicks' Dynasty Ceiling?
Ja'Tavion Sanders

a Sneaky Buy in Dynasty Leagues
Tank Dell

Steadily Regaining Dynasty Value
Paul George

Does a Little Bit of Everything in Game 2 Loss
Tyrese Maxey

Tallies Team-High 26 Points in Wednesday's Loss
Jalen Brunson

Leads Knicks With 26 Points Wednesday
Victor Wembanyama

Notches Another Double-Double
Stephon Castle

Scores Game-High 21 Points in Blowout Win
Ayo Dosunmu

Exits Game 2 With Heel Issue
OG Anunoby

Suffers Apparent Leg Injury Wednesday
Mark Stone

Nets Late Power-Play Goal in Losing Effort
Leo Carlsson

Pots Game-Winner Wednesday Night
Juraj Slafkovsky

Ends Point Drought in Game 1 Loss
Bowen Byram

Ties Franchise Record With Fourth Postseason Goal
Zach Benson

Posts Second Consecutive Multi-Point Game
Rasmus Dahlin

"Seems Fine" After Early Exit on Wednesday
Sam Merrill

Listed as Questionable for Thursday
Geno Smith

Frank Reich Says Geno Smith is the "Perfect Fit" for his Offense
Aaron Rodgers

Cardinals Interest in Aaron Rodgers Isn't Real
Luke Kennard

Tagged as Questionable for Game 2 Against Thunder
Travis Hunter

Expected to Play Both Ways in Year 2
Jarred Vanderbilt

Considered Doubtful for Thursday
Jalen Williams

Still Out Thursday
Carter Bryant

Available Wednesday Night
Luka Dončić

Luka Doncic Reveals Recovery Timeline
Anthony Edwards

Cleared for Game 2 Against Spurs
Mitchell Robinson

is Ruled Out for Game 2 on Wednesday
Kevin Huerter

is Doubtful for Game 2 on Thursday
Brandon Miller

has Successful Shoulder Surgery
Emilio Pagán

Emilio Pagan has Grade 2 Hamstring Strain, Expected to Miss 4-8 Weeks
Ayo Dosunmu

is Cleared to Play in Game 2
Joe Ryan

Listed as Scheduled Starter for Saturday Against Cleveland
Joel Embiid

is Downgraded to Out for Game 2
Tyler Glasnow

Not Expected to Land on the Injured List
Framber Valdez

Suspension Reduced to Five Games
Nils Hoglander

Will Miss World Championship Due to Injury
Christian Dvorak

Likely to Play in Game 3 Against Hurricanes
Owen Tippett

a Game-Time Decision Thursday
Noah Cates

to Miss Rest of Round 2
Arber Xhekaj

Rejoins Canadiens Lineup Wednesday
Brendan Gallagher

Scratched on Wednesday
Logan Stanley

Returns to Action Wednesday
Framber Valdez

Suspended Six Games
Tyler Glasnow

Exits Early on Wednesday With Back Pain
Russell Wilson

Jets Offer a Contract to Russell Wilson
CFB

Brauntae Johnson the Next Star in Notre Dame's Secondary?
CFB

Ethan Barbour a Name to Know in Georgia's Tight End Room
CFB

Payton Pierce Next Up at Linebacker for Ohio State
CFB

Javin Gordon to Play Significant Role for Tennessee?
CFB

Tanook Hines Stepping into WR1 Role for USC
CFB

Rueben Owens II has "Star Potential" in Fourth Campaign
Brandon Woodruff

has Fluid Drained From his Right Shoulder
Brandon Woodruff

to Resume Throwing on Saturday, Return Imminent?
Carlos Correa

to Have Season-Ending Ankle Surgery
Jacob Misiorowski

Listed as Friday's Probable Starter
Logan Webb

Dealing With Knee Discomfort
Carlos Correa

Expected to Miss Significant Time With Ankle Injury
Collin Morikawa

Withdraws From Truist Championship
Xander Schauffele

Carries Elite Form Into Quail Hollow
Hideki Matsuyama

Looks to Bounce Back at Truist Championship
Matt Fitzpatrick

Secures Third Win of 2026 Season
Patrick Cantlay

Continues Playing Well Heading to Truist Championship
Ludvig Aberg

Returns to Action For Truist Championship
Justin Thomas

Searching for Consistency at Quail Hollow
Jordan Spieth

Looks to Break Through at Quail Hollow
Adam Scott

Brings Strong Form to Quail Hollow
Robert MacIntyre

a Steady Option at Truist Championship
Jason Day

Looks to Overcome Approach Struggles at Quail Hollow
Akshay Bhatia

Looks for Complete Game at Truist Championship
Chet Holmgren

Leads Thunder to Victory in Game 1 Against Lakers
LeBron James

Scores Game-High 27 Points in Tuesday's Loss
Mats Zuccarello

Extends Point Streak to Five Games
Kirill Kaprizov

Nets Third Playoff Goal
Scott Wedgewood

Returns to Form in Game 2 Against Wild
Gabriel Landeskog

Picks Up Two Power-Play Points Tuesday
Martin Necas

Has Second Straight Multi-Point Outing
Nathan MacKinnon

Joins Exclusive List With Another Three-Point Performance
TOR

Maple Leafs Win Draft Lottery
Emilio Pagán

Emilio Pagan Headed for Injured List With Hamstring Injury
Emilio Pagán

Emilio Pagan Carted Off With Apparent Hamstring Injury on Tuesday
Justin Rose

to Continue Mid-Season Club Change at Truist Championship
Si Woo Kim

is Back to Peak Form Ahead of Truist Championship
Sam Burns

to Bounce Back at Truist Championship
Cameron Young

Looks to Carry Dominance to Quail Hollow
Rory McIlroy

Returns to Familiar Stomping Grounds This Week at Quail Hollow
Chris Gotterup

Looking to Bounce Back at Quail Hollow
MLB

Cardinals-Brewers Game Postponed on Tuesday
Roman Anthony

Day-to-Day With Wrist Sprain
Radko Gudas

to Remain Sidelined Wednesday
Jacob Misiorowski

"All Things Look Good" for Jacob Misiorowski to Start on Wednesday
Tommy Fleetwood

Looking For Better Iron Play at Quail Hollow
MLB

Rockies-Mets Game Postponed Due to Inclement Weather
CFB

Mario Craver Enters No. 1 Wide Receiver Role for Marcel Reed
Raisel Iglesias

Braves Officially Reinstate Raisel Iglesias From Injured List on Tuesday
CFB

LaNorris Sellers a Strong Rebound Candidate in 2026
CFB

Cam Coleman Poised for Monster Year at Texas?
CFB

Will Hammond Pushing to Be Ready for Week 1
Alex Fitzpatrick

Looking to Keep Up Ball-Striking Output at Quail Hollow
CFB

Notre Dame Leads College Football in Returning Snaps
CFB

Two Ole Miss Football Players Arrested, Charged with DUI
Ben Griffin

Looks Solid on the Surface Heading to Charlotte
Chase Elliott

Earns his Second Texas Motor Speedway Victory
Denny Hamlin

Misses Out on Winning at Texas
Alex Bowman

Finishes Third for the Second Week in a Row at Texas
Tyler Reddick

Earns Seventh Top-Five Finish of the Season at Texas
Chris Buescher

Scores his First Career Texas Finish in the Top Five
CFB

Bryce Underwood in Better Situation Entering Sophomore Season
CFB

Nico Iamaleava Emerging as Leader, Playmaker for UCLA
Jack Della Maddalena

Gets Dominated At UFC Perth
Carlos Prates

Shines At UFC Perth
Beneil Dariush

Suffers A First-Round TKO Loss
Quillan Salkilld

Remains Unbeaten In The UFC
Tim Elliott

Drops Decision At UFC Perth
Steve Erceg

Wins Back-To-Back Fights
Ollie Schmid

Suffers First-Round TKO Loss
Marwan Rahiki

Remains Unbeaten
Christopher Bell

Is Christopher Bell Worth Rostering for Texas Lineups?
William Byron

Might have the Speed to Compete for the Win at Texas
Joey Logano

Provides Solid Upside for Texas DFS Lineups
Chase Briscoe

Could Chase Briscoe be A Sneaky Pick for Texas Lineups?
Ty Gibbs

Should DFS Managers Roster Ty Gibbs at Texas?
Daniel Suarez

Is Daniel Suarez Worth Rostering After Career-Best Starting Position at Texas?
Kyle Busch

Is a DFS Risk Starting in the Top 10 at Texas
Tyler Reddick

One of the Favorites to Win at Texas
Chase Elliott

Could Contend for Another Win at Texas
Carson Hocevar

on Pole at Texas
NASCAR

Bubba Wallace Wrecks in Practice at Texas
Chris Buescher

Looking to Continue Strong Run at Texas
Austin Dillon

Blows Engine in Practice at Texas
RANKINGS
C
1B
2B
3B
SS
OF
SP
RP

RANKINGS

QB
RB
WR
TE
K
DEF