For the first time since 2021, a Red Sox-Yankees series carries weight that goes beyond history or trash-talk.

Boston comes in at 81-66.

New York comes in at 81-65.

A half-game separates them, and every out this weekend will echo toward October.

What makes this series even bigger: if these two face off in the wild card round, the higher seed hosts all three games of that best-of-three series.

Three games, one park.

When September is all said and done, we could be looking at a wild card round set for either Kenmore Square or the South Bronx. And in all likelihood, we’ll be looking back on this weekend as the one that determined the setting for this hypothetical postseason meeting between baseball’s most bitter rivals.

This is what it’s all about.

Another chapter in the book.

Red Sox. Yankees. Let’s go.

Outside of the obvious home field that could be hanging in the balance, here are some of the biggest storylines heading into what should be an electric weekend at Fenway Park:

The Arms Race: Matchups That Could Define October

Here are the starting pitchers slated for each team heading into the weekend, as well as what each of them brings to the table:

Friday: Lucas Giolito vs. Luis Gil

- Giolito (10–3, 3.38 ERA) has not only been Boston’s surprising steady hand this season behind Garrett Crochet, but he’s someone who has elevated his game when pitching at Fenway Park. We’ll see if that Fenway magic can continue in what is without a doubt his biggest game as a member of the Red Sox to date.

- Gil (3–1, 3.31 ERA) has endured an up-and-down 2025 season, flashing the electric stuff that made him a breakout star in 2024 while also struggling with command and consistency as his innings piled up. Against Boston this weekend, Yankee fans will hope his swing-and-miss fastball can neutralize the patient approach of the Red Sox, though his recent control issues make him a high-variance wild card.

Saturday: Brayan Bello vs. Max Fried

- Bello has been one of the breakout stars of the 2025 Red Sox, posting an 11-6 record with a 3.12 ERA across 152.2 innings pitched. He’s compiled 114 strikeouts and is sporting a 1.21 WHIP. Maybe most important of all for the 26-year-old, he’s shown durability and a consistently steady performance after a disappointing season in 2024. He’s been especially effective against New York in his career (5-3, 1.95 ERA), so expect him to try and lean on that confidence this weekend in vintage Bello fashion.

- Fried has been one of New York’s most reliable starters in 2025, going 16-5 with a 3.02 ERA, 163 strikeouts, and a 1.10 WHIP over 176 innings pitched. Against the Red Sox in his career, Fried is 2-1 with an ERA around 2.16 in four appearances. And for those who follow the hot stove season, we all know Fried was someone on Boston’s radar before receiving an eight-year, $218 million deal with New York.

Sunday: Garrett Crochet vs. Will Warren

- Crochet has been one of MLB’s best starters in 2025. He’s 15-5 with a 2.57 ERA, 1.05 WHIP, raking up a league-leading 228 strikeouts over 185.1 innings. And the good news for Red Sox fans is that he’s proven more than capable of dominating New York. In their August matchup, he threw seven solid innings while striking out 11 in a 12-1 win. A gem on Sunday would be an exclamation point on a superb first season in Boston, with the chance of possibly giving him his “Cy Young moment” as the race remains tight with Detroit’s Tarik Skubal (13-4, 2.10 ERA).

- Warren has gone 8-6 this season with a 4.22 ERA, 158 strikeouts, and a 1.35 WHIP over 147 innings, showing durability as he’s logged the most starts in MLB this year. For New York to have a chance in the series finale, he’ll need to limit hard contact and avoid falling behind in counts. Boston’s lineup has a knack for turning mistakes into extra-base hits, so Warren’s ability to induce weak contact and manage runners on base will be central to his success.

Boston Strong vs. New York: Not Just a Fluke

Boston hasn’t just edged out the Yankees in 2025, they’ve thoroughly taken control.

In case you haven’t been paying attention, the Red Sox are currently 8-2 against the Yankees on the year.

They’ve won in close games, they’ve won in blowouts, and they’ve won at both Yankee Stadium and Fenway Park. Name the type of game and name the field, and the Red Sox have taken care of business against their biggest rival.

Offensively, Boston has consistently produced in these matchups, with their batting average (.264), extra-base hits (36) and slugging percentage (.451) all higher against the Yankees than their season averages against everyone else.

For my money, the most impressive offensive number for Boston vs. New York this season is their run differential, outscoring the Bronx Bombers 56-38 in 2025.

Here's the results of their 10 games so far:

- 6/6/25, 9-6 loss @ NYY

- 6/7/25, 10-7 win @ NYY

- 6/8/25, 11-7 win @ NYY

- 6/13/25, 2-1 win @ BOS

- 6/14/25, 4-3 win @ BOS

- 6/15/25, 2-0 win @ BOS

- 8/21/25, 6-3 win @ NYY

- 8/22/25, 1-0 win @ NYY

- 8/23/25, 12-1 win @ NYY

- 8/24/25, 7-2 loss @ NYY

The bats have risen to the occasion in these matchups, and they’ll need them to do so again this weekend.

A Mini Playoff Series

We’re going to find out a lot about Giolito, Bello and Crochet over the next three days.

Two of these three guys have never pitched in truly meaningful games this late into a season, and the one who has (Giolito) hasn’t done so since 2021 - where he gave up 4 runs over 4.1 innings while allowing 3 hits and 5 walks.

This isn’t just another rivalry weekend, it’s an October dress rehearsal for these arms.

A series-win here for either team could shape the playoff bracket, the atmosphere, even the margin for error down the stretch.

Boston needs to grab this opportunity.

New York needs to defend it.

A Brief Flashback to 2021

The last time Red Sox-Yankees baseball felt this consequential was October 5, 2021, when the two collided in a winner-take-all AL Wild Card Game at Fenway Park.

Both clubs had clawed their way to matching 92-70 records, forcing a frantic final weekend that saw Boston sweep Washington and the Yankees squeak past Tampa Bay to set up a showdown the MLB league office was surely thrilled by.

The game itself was pure theater:

Xander Bogaerts launched a two-run shot off Gerrit Cole in the first inning, Rafael Devers added insurance late, and Nathan Eovaldi spun 5.1 electric innings as Fenway roared.

Boston walked away with a 6–2 win, sending the Yankees home stunned and igniting a brief but unforgettable Red Sox postseason run.

That was the last time Fenway saw postseason action.

If Boston takes care of business this weekend, it will help ensure a return of October magic to baseball's oldest ballpark in 2025.

First pitch on Friday is set for 7:10 p.m. ET on Apple TV+.

(go help your parents and grandparents get set up ahead of time, and be ready for a phone call at 7:08 asking you to repeat everything you already showed them in person earlier that day)

Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a digital content producer for WEEI.com, and a native of Lincoln, RI.