Yankees vs. Red Sox Prediction, Odds, Probable Pitchers, Prop Bets for Tuesday, April 21

One of the best rivalries in Major League Baseball takes center stage on Tuesday night, as the Boston Red Sox host the New York Yankees for the first time in the 2026 season.

Boston is off to a slow start in the 2026 campaign, but it picked up a win over the Detroit Tigers on Marathon Monday, a step in the right direction ahead of this rivalry matchup.

New York is currently in first place in the AL East after sweeping the Kansas City Royals over the weekend. The Yankees are set as small underdogs in this matchup, as two young starting pitchers will take the mound.

Luis Gil (7.00 ERA) is making his third start of the season for New York, and he’s looking to rebound after two shaky outings to start 2026. He’ll match up against Connelly Early (2.29 ERA), who is making his fifth start of the season for Boston.

Early picked up his first win of 2026 in his last outing, tossing six innings of two-hit, one-run ball against the Minnesota Twins.

Here’s a look at the odds, a player prop to consider and my prediction for this AL East battle on April 21.

Yankees vs. Red Sox Odds, Run Line and Total

Odds via DraftKings Sportsbook

Run Line

Yankees -1.5 (+158)
Red Sox +1.5 (-192)

Moneyline

Yankees: -102
Red Sox: -118

Total

8.5 (Over -105/Under -115)

Yankees vs. Red Sox Probable Pitchers

New York: Luis Gil (0-1, 7.00 ERA)
Boston: Connelly Early (1-0, 2.29 ERA)

Yankees vs. Red Sox How to Watch

Date: Tuesday, April 21
Time: 6:45 p.m. EST
Venue: Fenway Park
How to Watch (TV): TBS
Yankees record: 13-9
Red Sox record: 9-13

Yankees vs. Red Sox Best MLB Prop Bets

Yankees Best MLB Prop Bet

Aaron Judge 2+ Hits, Runs, RBIs (-139)

Aaron Judge is starting to find his groove, raising his average from .125 to .232 in the month of April, and he’s starting to contribute across the board for the Yanks, hitting nine home runs and driving in 16 runs over his first 22 games.

Judge has two or more hits, runs and RBIs in 10 of his games this month, and he’s taking on a youngster in Early who has an expected batting average against of .252 in the 2026 season.

The reigning AL MVP could clear this prop with one swing on Tuesday, and he’s picked up at least one hit in 12 of 16 April games. That gives him a really solid floor when it comes to this series opener.

Yankees vs. Red Sox Prediction and Pick

Earlier today, I shared in SI Betting’s MLB Best Bets column why I’m betting on Boston to win the first five innings of this matchup:

Boston’s off to a slow start in the 2026 season, but it may have an early advantage on the mound against the Yankees on Tuesday.

Connelly Early has allowed two or fewer runs in each of his four starts this season, posting a 2.29 ERA. He’s coming off his best start of the season, tossing six innings of two-hit ball in a win over the Minnesota Twins.

Now, he takes on Luis Gil, who has struggled in limited outings for New York in 2026. Gil has a 7.00 ERA across two starts, allowing eight hits, seven runs and five walks in just 9.0 innings of work. He ranks in the 12th percentile in MLB in expected ERA (6.40), the 12th percentile in hard-hit percentage and the 13th percentile in barrel percentage.

Even though Early’s advanced numbers aren’t great – he’s in just the 24th percentile in expected ERA – the Yankees are just 17th in OPS and 28th in batting average against left-handed pitchers this season.

I wouldn't be shocked if Boston is leading this game before the bullpens take over on Tuesday.

Pick: Red Sox First 5 Innings Moneyline (-125 at DraftKings)

Odds refresh periodically and are subject to change.

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