Brewers vs Rays Best Bets, Expert Picks & World Series Game 5 Predictions Tonight

Jason Wilson - Betting Analyst at Covers.com
Jason Wilson • Betting Analyst 19+ years betting experience
Updated: Oct 28, 2026 , 11:11 AM ET • 4 min read

Even if Jacob Misiorowski doesn't pitch deep into Game 5 of the World Series, a couple of our MLB experts are backing the Brewers tonight against the Rays.

Brewers vs Rays Best Bets and Expert Picks. Jacob Misiorowski Chandler Simpson
Photo By - Reuters Connect. Custom image of Brewers ace Jacob Misiorowski and Rays outfielder Chandler Simpson

After an improbable comeback extended the World Series to a fifth game, our Brewers vs. Rays expert picks are back for more on Wednesday, Oct. 28.

Our analysts are offering their top MLB picks for what once again may be our final slice of baseball until spring.

Brewers vs Rays expert picks for Game 5

Pick Probability
Josh Inglis Josh Inglis: Jacob Misiorowski u15.5 outs 53%
Joe Osborne Joe Osborne: MIL ML 57%
Neil Parker Neil Parker: William Contreras o1.5 H+R+RBI 51%
Dustin Saracini Dustin Saracini: Chandler Simpson o1.5 H+R+RBI 44%

Probabilities courtesy of Polymarket. For help understanding Polymarket probabilities, see our odds calculator.

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Josh Inglis' expert pick: Jacob Misiorowski Under 15.5 outs

Price: 53¢ at Polymarket

I have this priced at 60%, and the odds are already dropping. The Tampa Bay Rays have seen Jacob Misiorowski once, and the 24-year-old might be running on fumes. He's thrown 13 1/3 postseason innings on top of 174 2/3 during the regular season after logging just 130 frames in 2025.

He's been laboring through his playoff starts and threw just 78 pitches in Game 1 of the World Series. He hasn't recorded more than 15 outs in any of his three postseason starts, and the familiarity edge now shifts toward Tampa.

Even with a good outing, I see five innings as his ceiling. At 53%, there's still value in backing the Under.

Joe Osborne's expert pick: Brewers moneyline

Price: 57¢ at Polymarket

The Milwaukee Brewers are 12-0 in Misiorowski’s last 12 starts and 23-4 since May 1.

Milwaukee also owns the bullpen edge this World Series: a 1.29 ERA compared to Tampa Bay’s 4.12, and another reliever-heavy night looms for the Rays after using six pitchers in Game 3 and seven in Game 4.

At the plate, Milwaukee’s .773 series OPS dwarfs Tampa’s atrocious .491.

With an elite starter, a stronger bullpen, and a more productive lineup, I’m backing the Brewers to finish the job tonight

Neil Parker's expert pick: William Contreras Over 1.5 hits + runs + RBI

Price: 51¢ at Polymarket

Even with a 0-for-5 night at the dish in Game 4, Milwaukee catcher William Contreras has gone 7-for-17 with a run and three RBI during the World Series.

He’s sporting a .454 wOBA for the postseason while hitting in the heart of the lineup, so I recommend this Over up to 55%. Contreras posted a nearly identical .760 OPS against left-handed pitchers and .756 OPS against righties during the regular season, too

Dustin Saracini's expert pick: Chandler Simpson Over 1.5 hits + runs + RBI

Price: 44¢ at Polymarket

I'd play this up to 48%.

Chandler Simpson has been one of the Rays' most reliable bats throughout the World Series. He's recorded at least one hit in five of his last six postseason games, highlighted by a three-hit performance in Game 4.

He played a pivotal role in Tampa's two-run comeback in the 12th inning, continuing to deliver the goods for a team that's largely been counted out.

He's 3-for-5 against the Miz in his career, and at this price, you have to make that trade


How to watch Brewers vs Rays Game 5

Location Tropicana Field, St. Petersburg, Fla.
Date Wednesday, Oct. 28, 2026
First pitch 8 p.m. ET
TV FOX

Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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Jason Wilson Covers.com
Betting Analyst

Jason Wilson is an experienced journalist who has worked in a variety of roles within the industry for the past 18 years. Working at community newspapers in New Brunswick, Jason wore many hats as a reporter, editor, and photographer, covering everything from sports to courts to municipal politics. After shifting gears and working as an educator for a few years in the 2010s, Jason returned to full-time work in media as an MLB news editor for six years at theScore in Toronto before joining Covers in late 2021.

He has honed his editorial acumen over his years in the industry, showcasing flexibility, patience, and a strong work ethic. While he was relatively new to sports betting upon joining Covers, Jason has taken the plunge with gusto to learn the ins and outs of the industry, both as a method to improve professionally and to add an extra angle to his sports fandom.

In addition to sports, Jason is an avid film nut and former movie critic who monitors the Academy Awards betting odds for Covers. Jason holds a Bachelor of Arts in journalism degree and a Bachelor of Education degree from St. Thomas University.

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