Free Major League Baseball Predictions for May 29

Steve Seagrave

Event: (915) Los Angeles Angels at (916) Tampa Bay Rays: Mike Trout Hits + Runs + RBIs

Sport/League: MLB

Date/Time: May 29, 2026 7:10 PM EDT

Free Major League Baseball Pick Today: Mike Trout Hits + Runs + RBIs Over 1.5 (-105) Home Listed Pitcher Must Start

Mike Trout Hits + Runs + RBIs Over 1.5 (-105) Home Listed Pitcher Must Start:

Mike Trout has covered this HRR line in 5 of his last 7 games after going 2-3 with a couple of doubles and free passes in his last game against the Detroit Tigers. Now Trout gets another crack at Nick Martinez who he's gone 7-25 (.280) against with two home runs and three free passes. Martinez has posted an impressive 1.51 ERA and 1.11 WHIP but his underlying metrics tell us that he's due for regression as his xERA sits at 4.25 with an xFIP of 4.30. The Tampa Bay starter is backed by a bullpen that ranks 21st in ERA on the season (4.39). Trout has historically dominated the Rays at Tropicana Field while boasting a career .308 batting average with 80 hits, 27 home runs and 56 runs scored across 73 games. The future Hall of Famer is slated to bat 2nd tonight in the Halos order and he'll be guaranteed a full 9 innings of at-bats against a pitcher that he's thrived against in the past.

*Playable at -125 or better

Released/revised 4 hour(s) ago

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David Delano

Event: (915) Los Angeles Angels at (916) Tampa Bay Rays: Moneyline

Sport/League: MLB

Date/Time: May 29, 2026 7:10 PM EDT

Free Major League Baseball Pick Today: Tampa Bay Rays -160 Action

Tampa Bay has been a money train this season, even though the Rays come in off four straight losses after getting swept on the road in Baltimore. The key is that all four of those losses came away from home. Now Tampa returns home, where it has been dominant at 19-5. Nick Martinez gets the ball and has been excellent in this park, going 2-0 with a 1.14 ERA at home this season. This is a strong bounce-back spot for a Rays team that should settle back in.

Urena is off to great start for the Angels, but based on his minor league track record, regression is on the way.

Take Tampa Bay on the moneyline.

Released/revised 6 hour(s) ago

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Jackie Mack

Event: (907) Chicago Cubs at (908) St. Louis Cardinals: Moneyline

Sport/League: MLB

Date/Time: May 29, 2026 7:15 PM EDT

Free Major League Baseball Pick Today: Chicago Cubs -130 Action

The Cardinals have started to show regression and are in a losing slump as their offense runs hot and cold. Their pitching can be exploited as it gives up more runs now. The Cubs have started to turn the corner and can continue their new success with Imanaga on the mound who has been stellar so far. The Cubs have the much better lineup, better defense and pitching, so look for them to get another win today.

Bet: take the Chicago Cubs on the moneyline.

Released/revised 7 hour(s) ago

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Terry Edelmann

Event: (917) Boston Red Sox at (918) Cleveland Guardians: Travis Bazzana Bases

Sport/League: MLB

Date/Time: May 29, 2026 7:10 PM EDT

Free Major League Baseball Pick Today: (CLE) Travis Bazzana Over 1.5 Bases (+138) Action

This is a 2⭐️PLAY

Play: (CLE) Travis Bazzana Over 1.5 Bases (+138) at Draftkings

Travis Bazzana enters tonight’s home matchup against the Boston Red Sox in spectacular form, making him an elite target to clear his total bases prop. The rookie second baseman has cashed his Over on Total Bases in five consecutive games, adjusting rapidly to big-league pitching. Bazzana has been particularly dominant at Progressive Field, carrying an active trend where he has hit for multiple bases in six of his last seven home games. Adding to his value, hitting conditions in Cleveland will be pristine: clear skies, a warm 77°F at first pitch, a low 36% humidity, and zero threat of rain. Back the red-hot rookie to keep his foot on the gas and exploit his home-field advantage early.

Released/revised 7 hour(s) ago

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Joe Duffy

Event: (921) Kansas City Royals at (922) Texas Rangers: Total

Sport/League: MLB

Date/Time: May 29, 2026 8:05 PM EDT

Free Major League Baseball Pick Today: Total Under 7.5 (-112) Action

When comparing today’s total to the total in at least one of the starters’ previous starts, produces an under angle of 2220-1855-200. Total less than each pitchers’ last start goes under 685-504-57.

Released/revised 8 hour(s) ago

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Bryan Power

Event: (927) Milwaukee Brewers at (928) Houston Astros: Moneyline

Sport/League: MLB

Date/Time: May 29, 2026 8:10 PM EDT

Free Major League Baseball Pick Today: Milwaukee Brewers -118 Coleman Crow (RHP), Kai-Wei Teng (RHP) Must Start

A couple things you should note before we get into the specific matchup. Milwaukee has a rest edge here (they didn't play Thursday) and the National League is an incredible 34 games above .500 in Interleague play this season.

The Brewers aren't just "any old NL team." They're one of the best teams in all of baseball (top four in my power ratings) and the price on them is just way too cheap (IMO) for Friday's series opener in Houston. This is a team that's now won 15 of 19 and just swept St. Louis earlier in the week.

So why are we able to grab the Brew Crew at such a short ML price? Perhaps it's because Kai-Wei Teng, the starter here for Houston, has not given up a run in B2B starts. But Teng's xERA still sits more than a full run higher than his actual ERA. The Astros' bullpen has the highest ERA in all of MLB. So I think Milwaukee should be able to put up a "crooked number" tonight and move to a perfect 3-0 this season when Coleman Crow starts.

Released/revised 9 hour(s) ago

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Marc David

Event: (909) San Francisco Giants at (910) Colorado Rockies: Total

Sport/League: MLB

Date/Time: May 29, 2026 8:40 PM EDT

Free Major League Baseball Pick Today: Total Under 10.5 (-103) Logan Webb (RHP), Michael Lorenzen (RHP) Must Start

Marc David Sports' Free Pick

We really like the under in this matchup. San Francisco’s offense has hovered near the bottom of MLB in runs per game this season, and the Rockies have averaged only three runs per game over their last 10. While Coors Field is always tricky, they are just 6–10–1 to the over/under in home games with totals of 10.5 or higher.

Giants ace Logan Webb has been outstanding against Colorado, going 11–3 with a 2.97 ERA in 19 career outings, and he has plenty of experience navigating Coors Field and how to avoid full-scale blowups.

Value to -120.

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Released/revised 11 hour(s) ago

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For a limited time, get every baseball play from your favorite handicapper for three full days — and any 5% Best Bets released — for just $49. That's only $16.33 per day for every premium baseball release your handicapper posts. You'll receive instant access the moment plays are released, ensuring you get the best possible number before the lin ...

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Mike Lundin

Event: (917) Boston Red Sox at (918) Cleveland Guardians: Moneyline

Sport/League: MLB

Date/Time: May 29, 2026 7:10 PM EDT

Free Major League Baseball Pick Today: Cleveland Guardians -119 Action

Red Sox vs Guardians MLB Free Pick

The Angle(s): The Cleveland Guardians have been of the most profitable teams to back in 2026, while we find Boston Red Sox on the other end of the spectrum as one of the best fades. The Red Sox are 6-12 as underdogs and fading them in these spots have generated a +17% ROI. Cleveland has won four of Slade Cecconi's last five starts, and he's been rock solid at home all season. Boston turns to Tyler Samaniego as an opener for Brayan Bello (2-5, 6.43 ERA) who clearly is having a tough season.

The Bet: GUARDIANS (3%). 

Bet to: Guardians -135.

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Released/revised 13 hour(s) ago

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For a limited time, get every baseball play from your favorite handicapper for three full days — and any 5% Best Bets released — for just $49. That's only $16.33 per day for every premium baseball release your handicapper posts. You'll receive instant access the moment plays are released, ensuring you get the best possible number before the lin ...

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Bruce Marshall

Event: (919) Detroit Tigers at (920) Chicago White Sox: Moneyline

Sport/League: MLB

Date/Time: May 29, 2026 7:40 PM EDT

Free Major League Baseball Pick Today: Chicago White Sox 106 Action

An overreaction, we suspect, in the marketplace to this pitching matchup at the Rate, with so little confidence in Chisox starter Erick Fedde after a succession of bumpy outings and his 5.47 ERA. Will Venable, however, will have a quick hook and several capable relievers at the ready.

Meanwhile, perhaps too much respect granted Detroit's Troy Melton, who worked five good innings in his first start of the season on Sunday at Baltimore, though the frigid Tigers have lost 18 of 22 into tonight, and are just 8-21 away. Play White Sox on Money Line

Released/revised 14 hour(s) ago

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Ricky Tran

Event: (911) Philadelphia Phillies at (912) Los Angeles Dodgers: Moneyline

Sport/League: MLB

Date/Time: May 29, 2026 10:15 PM EDT

Free Major League Baseball Pick Today: Philadelphia Phillies 100 Zack Wheeler (RHP) Must Start

Ricky's play on PHI.

Key Angle: It's important to remember that Ricky never makes a bet on any game based on just one angle. In order to make the grade, all his premium picks must meet several important criteria. He doesn't share all his secrets within his analysis, instead he chooses to reveal only the angle that he feels is the most significant. Here in this game the recent history of these two teams is particularly significant.

- Philadelphia is 4-1 in its last 5 games.

- LA Dodgers is 1-4 in its last 5 games against an opponent in the National League East Division

- Philadelphia is 9-2 in its last 11 games against an opponent in the National League.

Verdict: The value is on the Road Underdog.

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Mike Fink

Event: (923) New York Yankees at (924) Oakland Athletics: Moneyline

Sport/League: MLB

Date/Time: May 29, 2026 9:40 PM EDT

Free Major League Baseball Pick Today: Oakland Athletics 126 Action

The Yankees have put together a few wins on their road trip and look to take over this game on the road. However, the A's are a tough out, and Luis Severino looks to take over this game against the team that drafted and developed him.

Released/revised 18 hour(s) ago

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