Walk-Off Wagers: MLB Best Bets Today (Predictions for Brewers-Red Sox, A’s-Astros and Pirates-D-Backs)

Breaking down the best bets for the MLB action on Wednesday, May 28, including a pick for Paul Skenes' start.

The Pirates-Diamondbacks game could be a low-scoring affair on Wednesday. / Charles LeClaire-Imagn Images

Pittsburgh Pirates ace Paul Skenes is one of many great pitchers on the mound for Wednesday’s loaded 15-game slate, and today is the second time this week where bettors can get in on the action early.

There are a bunch of afternoon starts in Major League Baseball on Wednesday ahead of a huge travel day, which gives us a chance to make some picks from 1:10 p.m. EST through the night games.

I’m eyeing three plays, including a couple of totals with some intriguing starting pitching matchups. 

With only four games scheduled for Thursday, Wednesday is a great time to get in on the MLB action.

Here’s a breakdown of my favorite bets for May 28, including several plays for the afternoon games on the slate. 

MLB Best Bets for Wednesday, May 28

Odds via DraftKings Sportsbook.

• Milwaukee Brewers First 5 Innings Moneyline (-154) vs. Boston Red Sox
• Pittsburgh Pirates-Arizona Diamondbacks UNDER 7.5 (-115)
• A’s vs. Houston Astros OVER 8.5 (-105)

Milwaukee Brewers First 5 Innings Moneyline (-154) vs. Boston Red Sox

The Milwaukee Brewers are aiming to sweep the Boston Red Sox on Wednesday afternoon, and they’ll have their ace on the mound to get it done.

Freddy Peralta (5-3, 2.55 ERA) will make his 12th start of the season, and he’s been really solid in 2025, allowing two or fewer earned runs in nine of his 11 starts. He’s allowed four or fewer earned runs in every start, and the veteran right-hander currently ranks in the 92nd percentile in pitching run value, 63rd percentile in expected ERA and 86th percentile in hard hit percentage.

He’ll take on Boston righty Brayan Bello, who has led the Sox to a 5-2 record in his seven starts despite a shaky 4.08 ERA and 4.88 Fielding Independent Pitching. Bello has allowed 12 runs over his last three starts, and he has failed to work through five innings in each of his last four outings.

The Red Sox have struggled offensively in this series, scoring just three runs overall. That is worrisome since Bello has not pitched well in 2025, ranking in the ninth percentile amongst all pitchers with an expected ERA of 5.50.

While I’d rather avoid the Milwaukee bullpen (4.61 ERA this season), I do think the Brewers will have the lead early on in this game. Peralta has been ultra-consistent on the bump, and Bello has failed to even get through five frames without some issue as of late.

This is an easy bet for the series finale in this interleague clash. 

Pittsburgh Pirates-Arizona Diamondbacks UNDER 7.5 (-115)

When Paul Skenes is on the mound, it’s hard not to bet on a Pittsburgh Pirates matchup.

The star pitcher has an insanely impressive 2.36 ERA this season despite the fact that the Pirates are just 4-7 in his starts. Skenes has given up two or fewer earned runs in nine of his outings, and he’s been lights out in the month of May, posting a 2.32 ERA across 31.0 innings of work.

On Wednesday, I’m eyeing the UNDER in the Pirates-Arizona Diamondbacks matchup, as Pittsburgh's offense has not given Skenes support all season long.

Not only do the Pirates rank dead last in MLB in runs scored and 29th in OPS, but they have scored four or fewer runs in nine of the 11 starts Skenes has made in 2025. 

Things won’t be easy against Arizona’s Zac Gallen, who has been one of the better pitchers in baseball in recent seasons – despite a slow start in 2025. Gallen currently has a 5.25 ERA, but I think this is a prime bounce-back spot for the righty against one of the worst offenses in baseball.

I’ll trust Skenes to keep this Arizona offense in check, as six of his outings already in 2025 have combined for seven or fewer runs. 

A’s vs. Houston Astros OVER 8.5 (-105)

The A’s snapped a lengthy losing streak earlier this week, beating the Philadelphia Phillies on Sunday, but they find themselves as underdogs on the road against the Houston Astros in an afternoon matchup on Wednesday.

Houston has Lance McCullers Jr. on the mound in this game, and the righty has struggled overall in the 2025 season, posting a 6.57 ERA in four starts. McCullers has walked 10 batters in just 12.1 innings of work, and he’s failed to get through five innings in any of his outings.

He’ll take on A’s starter Luis Severino (4.11 ERA) who has struggled in the month of May. Severino has given up 25 hits and 14 earned runs in just 22.0 innings of work this month – good for a 5.73 ERA.

So, I’m eying in the OVER in this matchup, especially since the A’s have one of the worst bullpens in MLB, posting a 5.96 ERA this season (28th in MLB).

On top of that, the OVER is 29-22-4 in the A’s games, the third-best OVER mark in the league. 

If McCullers continues to struggle on the mound, this game could be a high-scoring one early on Wednesday afternoon.

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Odds refresh periodically and are subject to change.

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