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New York Yankees vs. Boston Red Sox prediction, pick for ...
Brendan O'Sullivan · 2026-06-27 · via DraftKings Network

Brendan O’Sullivan dives into his pick and prediction for the New York Yankees vs. Boston Red Sox game on Friday, June 26.

The Yankees and Red Sox play the second game of their four-game series on Friday, June 26.

New York is a -118 moneyline favorite, while Boston is -102 on DraftKings Sportsbook. The game total is set at over/under 8.5 runs.

Let’s get into a pick and prediction for this Yankees vs. Red Sox game.

Yankees vs. Red Sox prediction, preview

While the rivalry may not have the same intensity as it did in the early 2000s, Yankees vs. Red Sox will always draw attention. New York is visiting for a four-game series with this matchup marking the second of the bunch. Will Warren and Payton Tolle will share the mound on Friday night.

Tolle, a 23-year-old lefty in his second MLB season, is pitching to a 3.08 ERA. The numbers indicate he’s a fine starter, but he’s allowed at least three earned runs in three consecutive games, taking his ERA from 2.28 to the current 3.08. His best quality right now may just be his ability to pitch deep into games. He’s pitched at least six frames in seven of his 11 starts this year, including his season debut against the Yankees in April. Allowing three earned runs isn’t ideal, but it helps that the bullpen typically doesn’t need an early arrival in these cases.

His last three starts were against the Mariners, Blue Jays. and Rays. All three of these teams rank in the bottom 11 for total runs scored this season. The Yankees rank fifth overall, so this will be Tolle’s biggest test of late, even with Aaron Judge still sidelined. New York always remains a threat on offense even when the stars aren’t performing. Players like Jazz Chisholm Jr. and Paul Goldschmidt have stepped up lately, filling the gaps caused by injuries.

The Red Sox rank last in total runs which is a a delight for Warren. The right-hander has a 3.45 ERA, but he was better earlier this year. His starts have gotten shorter and less reliable, but he’s only had one terrible outing: May 6 vs. the Rangers. Every other start has either been messy due to unearned runs or short performances. A weak Boston team that struggles to score may be the remedy Warren needs.

Yankees vs. Red Sox Pick, Best Bet

The Yankees are on the road with Warren starting, so there’s reason to doubt the team in this position. That said, New York’s bullpen ranks fourth in ERA, just one spot below the Red Sox. With how the role players are performing in New York, another win should be coming to the pinstripes.

Best Bet: New York Yankees ML (-118)