Walk-Off Wagers: MLB Best Bets Today (Predictions for Tigers-Guardians, Padres-Cubs, Red Sox-Yankees)

Breaking down the best bets as the MLB playoffs begin on Tuesday, September 30.

Boston Red Sox pitcher Garrett Crochet will make his first career playoff start on Tuesday night. / John Jones-Imagn Images

The 2025 MLB playoffs start today!

We have four games on the docket as the playoffs get underway, giving us a full day of baseball action.

The Cleveland Guardians host the Detroit Tigers in a battle of AL Central teams to start the slate, and the Cincinnati Reds visit the Los Angeles Dodgers to close things out.

Let’s get right into the best bets – and their odds at the best betting sites – for Monday, September 29.

MLB Best Bets for Tuesday, Sept. 30

Odds via DraftKings Sportsbook

• Cleveland Guardians Moneyline (+135) vs. Detroit Tigers
• Chicago Cubs Moneyline (-118) vs. San Diego Padres
• Boston Red Sox Moneyline (+107) at New York Yankees

Cleveland Guardians Moneyline (+135) vs. Detroit Tigers

The Guardians finished off a historic comeback to win the AL Central by a game over these Tigers, and it’s only fitting that they face off in the Wild Card round.

Cleveland won five straight over Detroit in September before the Tigers salvaged a win in their final regular-season matchup. Two of those five wins – in back-to-back meetings – were against AL Cy Young Award favorite Tarik Skubal, who is scheduled to take the mound on Tuesday afternoon.

The southpaw has pitched well against the Guardians, allowing just four runs (two earned) in 28 innings across four starts, but his team only went 2-2 in those three games, including a loss as -200 favorites on September 18 and -150 on September 23.

Gavin Williams has been stellar for Cleveland as the Guardians have won each of his last five starts, including his last two both against the Tigers.

This isn’t a slam-dunk bet by any means, but there is no reason for the Guardians to be +135 as home favorites given how the season finished. Interestingly enough, the Guardians went 18-11 when the line was between +124 and +154 this season.

Chicago Cubs Moneyline (-118) vs. San Diego Padres

The San Diego Padres won seven of their final eight games, but must head on the road to face off against the Chicago Cubs.

The Padres went just 38-43 on the road this season, including 23-29 as road underdogs, while the Cubs were 50-31 at home (46-24 as home favorites). San Diego also finished under .500 (24-26) against teams with a winning percentage of .540 or higher.

Perhaps most importantly, this is a bet fading Padres starter Nick Pivetta. He went 5-4 with a 3.55 ERA and 1.14 WHIP on the road this season, including just a three-inning outing (six hits, three runs) at Wrigley Field back on April 5.

Given the struggles of both the team and pitcher on the road, and the Cubs’ success at home, Chicago is worth a bet at this low price.

Boston Red Sox Moneyline (+107) at New York Yankees

The Red Sox head into Yankee Stadium to face a red-hot New York squad. The Yankees have won eight straight and 11 of 12 games, but they didn’t exactly face the best competition.

In reverse order, the Yankees swept the Orioles and White Sox, took two of three in Baltimore, and two of three in Minnesota. Those are three of the bottom seven teams in the league. Sure, they can only play their schedule, and they did take care of business, but they could be in for a rude awakening against the Red Sox.

Boston won each of its last three series, taking two of three from Detroit, in Toronto, and in Tampa Bay. That was much-needed for the Sox, who dropped five of seven – including two of three to these Yankees – prior to that.

Still, the Red Sox won the season series 9-4 and are 23-9 when Garrett Crochet starts, undefeated in his last seven outings (two against New York). They’ve won all three of his starts against the Yankees this season, with him allowing five runs in 21.1 innings.

Max Fried is no slouch, and has pitched well against the Red Sox himself, but once again this feels like a game that should be closer to a coin flip. And the Yankees actually went 21-22 when the line was between -115 and -145; the Red Sox went 15-13 with the line -105 to +125.

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Odds refresh periodically and are subject to change.

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