Walk-Off Wagers: MLB Best Bets Today (Guardians Undervalued, Two Starters to Bet)

BetSided's Peter Dewey breaks down his favorite plays in Major League Baseball on May 27.
Cleveland Guardians pitcher Emmanuel Clase (48) and third base Gabriel Arias.
Cleveland Guardians pitcher Emmanuel Clase (48) and third base Gabriel Arias. / Gary A. Vasquez-USA TODAY Sports
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Happy Memorial Day baseball fans!

There’s a ton of afternoon baseball to enjoy during the holiday, and there are plenty of MLB bets to place in this matchup. 

I’m focusing mainly in the prop market for today’s slate, but there is one team that I believe is undervalued on the moneyline on the road. 

Let’s dive into these picks and hope for a Monday sweep!

Odds via DraftKings Sportsbook.

MLB Best Bets Today for May 27

  • Cleveland Guardians Moneyline (-130) vs. Colorado Rockies
  • Bryce Miller OVER 2.5 Earned Runs Allowed (+100)
  • Robert Gasser OVER 5.5 Hits Allowed (+100)

Cleveland Guardians Moneyline (-130) vs. Colorado Rockies

The Cleveland Guardians are on the road against the Colorado Rockies and lefty Austin Gomber.

Any time I see the Guardians matched up against a left-handed pitcher, I’m looking to take them to win. 

Cleveland is No. 2 in OPS this season against left-handed pitching, and Gomber, who has a 2.76 ERA, is due for some regression this season since he’s put up just a 4.59 Fielding Independent Pitching. 

Xzavion Curry will make his second start of the season for the Guardians, and he’s posted a 1.93 ERA across 9.1 innings of work. 

Ultimately, I’ll trust this Guardians team, which is in the mix to win the division this season, over the lowly Rockies on Monday. 

Bryce Miller OVER 2.5 Earned Runs Allowed (+100)

Seattle Mariners righty Bryce Miller has really struggled in the month of May, posting a 5.79 ERA in four starts, allowing at least two earned runs in each of those games. 

One of those starts came against the Houston Astros, where Miller allowed six hits and four earned runs across six innings. 

The young righty now has a FIP of 4.47 on the season, and I’m worried about him against a division rival that has already gotten to him this season. 

Until we see the Miller that was lights out in April, he’s a fade candidate at even money in this prop. 

Robert Gasser OVER 5.5 Hits Allowed (+100)

Milwaukee Brewers rookie Robert Gasser has pitched well this season, posting a 2.65 ERA in three starts, but he was knocked around by the Miami Marlins in his last outing, giving up 10 hits.

Gasser has allowed 16 hits in his last two starts, going over 5.5 hits in his last two games. I think he could be in line for more against the Chicago Cubs, even though they’re in the bottom 10 in the league in hits this season. 

Gasser doesn’t really have strikeout stuff, picking up just six over 17.0 innings in 2024, so the ball should be in play a lot on Monday.


Game odds refresh periodically and are subject to change.

Find Peter Dewey's betting record here You can also follow my daily plays on BetStamp here.