Best Bets for the 2021 World Series Matchup Entering the Stretch Run

By Dan Vasta in MLB
| August 19, 2021 8:23 am PDT

The 2021 MLB postseason brings more intrigue each year, but this one should be different. We go back to the five-team bracket per league after having eight last season.

The best-of-three series are luckily gone this season. The 2021 MLB postseason will be back to normal, allowing the fans to enjoy the game more than ever.

The Fall Classic is a yearly event that fans from across the country watch to cheer on their favorite team or league. There are a few dozen matchups that we could see in the World Series.

Predicting the exact World Series matchup is a challenge, but the rewards for accurately predicting it rank among the best MLB future wagers you could make. The best baseball betting sites will reward you for picking the two teams to play for it all.

Before you bet on the series itself, brush up on the history. Check out this World Series guide first.

The World Series has given us some dream matchups before, but here are your top World Series matchup picks for the 2021 stretch run.

5. Dodgers vs. Astros (+750)

The best baseball betting apps predictably have this one favored. Sign me up!

What a riveting matchup America would love to see again. Many would love a rematch from their epic 2017 World Series that came down to Game 7.

After Houston won it all, their cheating scandal did not go unnoticed and now they are the most unliked team in baseball.

Add Joe Kelly throwing at Carlos Correa with the benches clearing last season, and the rivalry has no love lost. The drama between these two would be bonkers if they ended up meeting with a World Series on the line.

Drama aside, this 2021 World Series matchup just makes sense. These two clubs are as accomplished as anyone since 2015.

Check out what they’ve both done since then.

Team Championship Appearances World Series Appearances
Dodgers Four Three
Astros Four Two

The odds on this matchup provide little value since many sportsbooks have this projection as the favorite.

Lady luck would need to be involved for these two to meet up, but it wouldn’t be a shocker. These are the two most potent offenses in the game, and their postseason experience could take them both to the top.

The pitching and number of aces that the Dodgers could throw at you is impressive. Max Scherzer, Walker Buehler, and Clayton Hershaw may dazzle in October.

The Astros aren’t too shabby with Zack Greinke and Lance McCuller Jr., so this matchup is worth a shot.

We have seen it once before, and chances are solid it could happen yet again.

4. Giants vs. White Sox (+2200)

The Giants may end up winning the NL West over the Dodgers despite nobody projecting such a result in the preseason. The pitching staff carried them in the first half of the season, but the offense has been productive.

The addition of Kris Bryant has put them over the top compared to most contenders.

All of their offensive pieces have mixed well together. Plus, they treat every game like the postseason. Taylor Rogers and Jake McGee have been tough to hit against this season, but they have hung on and survived many close games.

They may not have a true ace like some teams, but their rotation collectively has been one of the few elite teams in the league. The White Sox are a true contender due to their pitching staff.

Lance Lynn and Carlos Rodon could be the top duo of aces in the game, and they both have a shot at the AL Cy Young.

To see where exactly they rank among the contenders, be sure to check out our best bets for the 2021 Cy Young award.

The inconsistent offense for Chicago could be their weakness, but they have not had the majority of their regulars in the lineup together. By the time Labor Day rolls along or perhaps even sooner, they should start to heat up and be more of a threat.

The likes of Luis Robert and Eloy Jimenez did not see much time in the first half of the season.

White Sox Youngsters Luis Robert Eloy Jimenez
Games Played in First Half 25 0

The fact that Chicago got along just fine without them is pretty scary.

They have already made their marks in the second half now that they’re healthy, though. The pop they both bring to the everyday lineup for the White Sox gives them the potential to win it all. It was amazing to see what they did last season, but the 2021 second half has been kind to both.

This matchup is realistic since both are locks to join the best records in baseball, and it won’t be shocking if they each get the advantage of hosting games.

3. Dodgers vs. White Sox (+850)

The odds on this 2021 World Series matchup should arguably be better than they presently are.

The Dodgers would attempt a repeat as World Series champions, with the young upcoming White Sox in their way. Dominant and potent lineups, the storylines will be endless.

Tony La Russa against Dave Roberts is a great battle of the master of minds.

The odds are why you need to consider this wager. If Los Angeles wins the division, they could host all their critical postseason games at Dodger Stadium.

The odds are short, but many will argue these are the top teams in the league. The aces at the top of rotation are elite, but both lineups could start stud hitters in the bottom of the order.

Luis Robert has hit around seventh in the order since he has played for the White Sox. The Dodgers have had Cody Bellinger hit near the bottom of the order as well.

The White Sox may be lacking the postseason experience, but they did arrive last season. They could have been a top seed last season, had it not been for Ricky Renteria gagging games away with silly decisions.

La Russa was brought in to fix those issues, and his championship experience speaks for itself.

Just check out what he’s done in his career.

  • 3 ALCS titles
  • 3 NLCS titles
  • 3 World Series titles

That type of championship success shouldn’t go unnoticed. There is no denying La Russa’s age and old school approach, but all the guy has done is win.

It just might put the White Sox within reach of a title, and it very well could come against the Dodgers.

2. Brewers vs. Astros (+1600)

The odds of getting these two former NL Central foes together in the World Series will likely shorten as the postseason draws closer.

The lineup for the Astros in their home ballpark is tough to limit. Keeping the ball in the yard seems to be an impossible task when facing the following.

  • Carlos Correa – 19 HR
  • Jose Altuve – 25 HR
  • Yordan Alvarez – 22 HR
  • Kyle Tucker – 22 HR
  • Yuli Gurriel – 12 HR

Tack on a healthy Alex Bregman, and the Astros are an understandable problem at the plate.

Houston and Milwaukee both have great hitting parks. It would be a treat if the two meet up, so take advantage of the value before the odds lengthen up.

The value at +1600 is incredible due to the path the Brewers will likely have. They may not have the top record in the NL, but they should host the NL East division winner.

The Brewers will be favorites over any team that comes out of the NL East.

Whether it is the Phillies, Braves, or Mets, the Brewers will have an edge. Taking on a team from the NL West is likely to occur, but this is one of the rotations that will limit any potent offensive group.

With perhaps just one brutal battle standing between them and a trip to the 2021 World Series, betting on the Brewers vs. Astros stands out.

My Top World Series Matchup Pick

  • Brewers vs. White Sox

The Brewers and White Sox could be destined for the World Series this season. The number of aces we saw between the pair when they met up in July was impressive.

The White Sox have added a bevy of healthy bats since that series. The Milwaukee offense is waiting for Christian Yelich to return to his All-Star and MVP status, yet they have continued to pile up wins.

Earlier in the season, the odds were much longer, so perhaps you had already jumped on this trendy matchup. As the wins pile up and these two clinch their division sometime in the middle of September, the odds should shorten.

Jump on the White Sox vs. Brewers World Series matchup before the price changes.

There are other 2021 World Series matchups that I also have faith in occurring. I favor pitching and timely hitting. The Dodgers, Brewers, and White Sox are listed the most on these picks.

Those look like the four best rosters mixed in with their paths.

The Giants have been the top team in baseball for most of the season, but the road ahead will be a challenge. They will have to take on the Dodgers before an NLCS matchup. I love the Giants and feel they are right with those main four.

The only other team to consider are the New York Yankees and the Boston Red Sox if they finish the season on a high note. I left the Toronto Blue Jays off because at least one of these three AL East teams will miss the postseason.

There could be two that miss out on the fall party. The Yankees lineup has been impressive since Joey Gallo was acquired. October is nearly upon us, and the unimaginable often becomes a reality.

Lean with my five most likely World Series matchups so you can come out victorious. Of course, you’ll also want to consider all of the top 2021 World Series contenders before finalizing any bets.

2021 World Series Contender Odds Following the Trade Deadline

The MLB Trade Deadline is a crucial point in every season. This year was no different with tons of impactful trades. Teams must decide if they want to flip their players in favor of younger ones or better ones. That gave way to some MLB teams boosting their...

Read More



AUGUST Sportsbook of the Month
Welcome Bonus 50% up to $1,000
Read Review Visit Site
Back to top