Yankees vs. Red Sox Prediction, Odds, Probable Pitchers and Prop Bets for Sunday, Sept. 14

Betting odds, pick and prediction for the New York Yankees-Boston Red Sox matchup on Sunday night.

The Boston Red Sox are 20-9 when starting pitcher Garrett Crochet is on the mound this season. / Eric Canha-Imagn Images

The New York Yankees have gotten some revenge on the Boston Red Sox in their weekend series, taking the opening two games to set up a 2.5-game cushion on Boston in the AL wild card race.

However, Sunday night’s game is going to be a tough one for the Yanks, who are underdogs at the best betting sites for this matchup. 

Garrett Crochet (2.57 ERA) is on the mound for Boston, and he threw seven innings of one-run ball in a win over New York in their last meeting. The Yankees will counter with righty Will Warren, who has struggled a bit since the start of August.

Here’s a breakdown of the odds, my favorite player prop and a prediction for this rivalry matchup on Sunday night.  

Yankees vs. Red Sox Odds, Run Line and Total

Odds via DraftKings Sportsbook

Run Line

• Yankees +1.5 (-170)
• Red Sox -1.5 (+139)

Moneyline

• Yankees: +127
• Red Sox: -156

Total

• 7.5 (Over -110/Under -110)

Yankees vs. Red Sox Probable Pitchers

• New York: Will Warren (8-6, 4.22 ERA)
• Boston: Garrett Crochet (15-5, 2.57 ERA)

Yankees vs. Red Sox How to Watch

• Date: Sunday, Sept. 14
• Time: 7:00 p.m. EST
• Venue: Fenway Park
• How to Watch (TV): ESPN
• Yankees record: 83-65
• Red Sox record: 81-68

Yankees vs. Red Sox Best MLB Prop Bets

Red Sox Best MLB Prop Bet

• Trevor Story to Hit a Home Run (+594)

Earlier today, I shared in SI Betting’s best home run picks – Daily Dinger – why Story is a great long shot prop target on Sunday night: 

Boston Red Sox shortstop Trevor Story has 24 home runs in the 2025 season, and I love the matchup he has on Sunday night.

Story and the Sox are looking to avoid a sweep against the New York Yankees, and they’ll take on righty Will Warren (5.43 road ERA this season) in the matchup.

Warren allowed five runs in four innings in his last start against Boston, and Story is 2-for-5 with a homer, a double and three runs batted in against Warren in his career. Story also has homered 18 times against right-handed pitching this season.

While he hasn’t been super prone to the long ball this season, Warren has still given up 18 home runs in 30 outings in 2025. 

Yankees vs. Red Sox Prediction and Pick

Even though the Yankees have taken the opening two games in this series, I lean with Boston to take the series finale.

As I mentioned, Crochet was lights out against New York the last time these teams met, and he has led the Sox to a 20-9 record in his 29 starts in 2025.

Meanwhile, Warren has really struggled on the road this season, posting a 5.43 ERA in 15 starts. He allowed seven hits and five runs in just four innings in his last start against Boston, and New York is just 8-7 in his road starts in 2025.

Warren also has an ERA of 4.05 and a FIP of 5.10 since the beginning of July. I’m not sold on him beating Crochet with Boston looking to avoid a sweep to stay in the mix for the top wild card spot in the AL. 

Pick: Red Sox Moneyline (-156 at DraftKings)

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Odds refresh periodically and are subject to change.

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