What a dream scenario for MLB. With the Blue Jays winning on the final day of the regular season and locking up the AL East, we’re left with a Wild Card series between the Red Sox and the Yankees, arguably the two biggest rivals in North American sports.
This isn’t quite the early 2000s. We haven’t seen Pedro Martinez recently throw any old men around. Yet this is still a clash between two of the American League’s best teams — teams that have a higher aspiration than getting eliminated from the postseason before this weekend.
As you would expect, DraftKings Sportsbook has your betting needs covered for Game 1, which gets going at 6:08 p.m. ET. There’s literally hundreds of prop bets available, so allow me to narrow your options down to my favorite three.
Red Sox vs. Yankees Prop Bets for Game 1
Garrett Crochet 8+ Strikeouts (-119)
Here’s a good place to start. A strikeout prop for the guy that led all of MLB in strikeouts during the regular season (255). Garrett Crochet was an absolute monster in his first year with the Red Sox, and while there has to be some legitimate concern about his workload after tossing a career-high 205.1 innings, Crochet looked dominant in his most recent outing, tossing eight scoreless innings in Toronto last Wednesday. The left-hander was able to clear this prop in 19 of his 32 starts in 2025, including in three of his four matchups with the Yankees. That makes sense, especially given the swing-and-miss issues that New York’s lineup presents. When you’re the best home run hitting team in baseball, there’s got to be a trade off. For the Yankees, it’s been a massive 26.8% strikeout rate in September — the fifth-highest mark in the league. Crochet shouldn’t need more than six innings to make this a winner.
Max Fried Under 1.5 Earned Runs Allowed (+106)
To be completely honest, Max Fried doesn’t have the best track record of success in the postseason. You’ll probably remember that Fried surrendered eight hits and five earned runs in just two innings of work in his final start in a Braves uniform last October. But today is a new day. After a slight hiccup in the middle of the season, Fried finished 2025 with incredible form, maintaining a 1.55 ERA and a 2.32 FIP over his last seven outings — a stretch that started by tossing six scoreless innings against these very same Red Sox on August 22. I’d argue Boston presents an even easier matchup in the present. Since September 3, the team’s first game after losing Roman Anthony (oblique) to injury, the Red Sox are slashing .251/.312/.382 with an 89 wRC+. Boston’s 17 home runs within that span are also the fewest of an AL club. In the playoffs, if you can’t hit for power, you usually don’t hit at all.
Goldschmidt vs. Bregman – Most Total Bases: Alex Bregman (-118)
Maybe you’ll want to shy away from Alex Bregman props if the recent reports of illness are true, but him having nearly identical odds in a total bases matchup with Paul Goldschmidt is silly. Bregman is one of the sport’s most proven postseason performers and he’s feasted on left-handed pitching in his tenure in Boston, slashing .319/.421/.443 with a 139 wRC+ within the split. Don’t get me wrong, Goldschmidt has also been amazing against LHPs in 2025 — as evidenced by a .448 expected wOBA — but there are two variables that give Bregman the clear edge on Tuesday. First and foremost, Goldschmidt has only hit southpaws in 2025, and I’d assume he’ll be pinch-hit for at some point in this contest. Second, Goldschmidt hasn’t hit Crochet. The former NL MVP is just 2-for-15 in his career versus Boston’s ace, with two singles and five strikeouts.
