Monday is the calm before the storm. For the next six days, the Boston Red Sox will do battle with a pair of first-place teams to determine the outcome of their season.

Entering this week’s matchups with the Toronto Blue Jays and Detroit Tigers, the Red Sox own a one-game lead, plus the tiebreaker over both the Houston Astros and Cleveland Guardians in the wild card mix. As long as they don’t lose two games more than both Houston and Cleveland, Boston will punch its ticket to October,

The odds may be in the Red Sox’s favor, but they still need to take care of business — and maybe get just a bit of help along the way. These are the three keys for the Red Sox to secure a playoff spot with minimal stress:

Let’s face it: at this point, the offense is a wild card on a nightly basis. At best, you might get a couple of clutch home runs and/or a big inning fueled by the opposition (see: Friday night against the Tampa Bay Rays). But for the entire month of September, the lineup has been liable to enter sleep mode.

That puts a ton of pressure on the starting pitchers, and the two series have very different rotation looks. In Toronto, it’s the “big three” that’s carried Boston for most of the season in Lucas Giolito, Garrett Crochet, and Brayan Bello. At home against Detroit, it’s two lefties with four combined starts for the Red Sox in Kyle Harrison and Connelly Early, then possibly Giolito again on Sunday if the game matters.

No matter who’s on the mound for any given night, the Red Sox starter can single-handedly swing the team’s playoff odds drastically depending on his performance.

Someone needs to sweep Guardians-Tigers series

For the most part, the Red Sox’s needs on the out-of-town scoreboard are obvious this week. Every loss by the Guardians, Tigers, and Astros helps Boston. But the fact that Cleveland and Detroit play each other for three of each other’s six games muddies the waters.

If either team sweeps the series, it’s a huge boon to Boston. In fact, the Red Sox could clinch a playoff spot by winning two of three against Toronto if the Guardians get swept on their home field. On the other hand, the worst-case scenario is probably Cleveland winning two of three, which would leave the two Central teams tied heading into the final weekend.

Sep 19, 2025; Tampa, Florida, USA; Boston Red Sox third base Alex Bregman (2) hits a home run during the third inning against the Tampa Bay Rays at George M. Steinbrenner Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images / Kim Klement Neitzel-Imagn Images

A lot happened in the Tampa Bay series this weekend, but the most important development may have been Bregman, the Red Sox’s superstar third baseman, going 5-for-11 with a home run and four walks. That’s a 1.327 OPS for the series, after putting up a .452 mark in his previous 24 games.

Lots of players could step up and have big weeks, and the Red Sox would welcome it from all of them. But Bregman is the one who’s carried teams to the playoffs before. He’s the one the Red Sox paid $40 million to bring them back to October this year, and he’s the one who’s going to likely opt ouf of $40 million each for the next two years because he thinks he deserves a better deal in free agency.

If he wants to prove that last point, it really would behoove him to give the Red Sox the offensive leadership they need for six more games.

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