MLB Expert Picks & Baseball Predictions for Sept. 29

Jon Metler - Betting Analyst at Covers.com
Jon Metler • Betting Analyst 5+ years betting experience
Updated: Sep 29, 2026 , 08:42 AM ET • 4 min read

Our MLB expert picks celebrate the beginning of playoff baseball with a selection of predictions from today's slate, including a high-scoring bout in San Diego.

Manny Machado San Diego Padres MLB
Photo By - Reuters Connect. San Diego Padres thrid baseman Manny Machado (13) celebrates after hitting a three-run home run.

Playoff baseball is officially here and our MLB expert picks are along for the ride on Tuesday, Sept. 29.

Our analysts are eyeing the New York Yankees and Philadelphia Phillies to win straight up, while the Over is the most appealing play in San Diego tonight.

It's all part of our full slate of MLB picks as the postseason gets underway today.

MLB expert picks for today

Pick Probability
Jon Metler Jon Metler: NYY ML 56%
Neil Parker Neil Parker: PHI ML 37%
Joe Osborne Joe Osborne: CHC/SD o7.5 47%
Dustin Saracini Dustin Saracini: BOS/NYY u6.5 54%

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

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    Jon Metler's expert pick: Yankees moneyline

    Price: 56¢ at Polymarket

    Give me the New York Yankees in Game 1 at 56% on the moneyline at Polymarket, as I price them closer to a 60% favorite against the Boston Red Sox. With the probability gap on the Yankees and Cam Schlittler on the mound, I'm gladly hitting the button after being on the wrong end of his postseason masterclass against Boston last year.

    Payton Tolle is an extreme fly-ball pitcher, which can be a dangerous profile at Yankee Stadium with the short porch in right field. While Tolle is a lefty and New York is expected to feature a mostly left-handed lineup, he didn't dominate left-handed hitters this season. Lefties posted a .704 OPS against Tolle, compared to just .624 for right-handed hitters, making the Yankees' southpaw-heavy lineup less of a mismatch than it might initially seem.

    Check out Dustin Saracini's full Yankees vs. Red Sox predictions for Game 1.

    • Time: 8 p.m. ET
    • How to watch: NBC

    Neil Parker's expert pick: Braves moneyline

    Price: 64¢ at Polymarket

    With the Philadelphia Phillies rotation taxed after battling to their final game to secure a postseason berth, I’d recommend the Atlanta Braves moneyline to 68%.

    Additionally, Braves lefty Chris Sale has posted a 3.31 xERA and 3.29 xFIP through eight starts against the Phillies over the past three years. He also just ranked third in xFIP while allowing the eighth-lowest squared-up contact rate among qualified pitchers in 2026.

    Philly is expected to counter with a bullpen game featuring bulk work from lefty Jesus Luzardo and righty Andrew Painter.

    Luzardo returned from a shoulder injury for a relief inning Sunday, while Painter sports a discouraging 4.60 xERA and  4.55 xFIP on the road.

    This gives the Braves a sizable starting-pitching edge in Game 1.

    Check out Neil's full Phillies vs. Braves predictions for Game 1.

    • Time: 2 p.m. ET
    • How to watch: NBC

    Joe Osborne's expert pick: Cubs vs Padres Over 7.5

    Price: 47¢ at Polymarket

    Both lineups enter the playoffs in strong form, and each has had success against the opposing starter.

    The San Diego Padres rank second in OPS over the past two weeks and first against lefties. They have a combined .839 OPS in 108 at-bats against Matthew Boyd and smacked him around for eight earned runs in two games this season.

    The Chicago Cubs have a .906 OPS in 33 at-bats against Michael King, while their offense has been especially strong on the road and against righties.

    Both bullpens rank in the bottom half of MLB in ERA over the past two weeks, giving these offenses a chance to add runs late. The Over hit in five of their six regular-season meetings, and I’m backing another high-scoring game.

    Check out Todd Cordell's full Cubs vs. Padres predictions for Game 1.

    • Time: 10 p.m. ET
    • How to watch: Peacock

    Dustin Saracini's expert pick: Red Sox vs Yankees Under 6.5

    Price: 54¢ at Polymarket

    We have two aces on the mound who have dominated this matchup all year, and I would comfortably play this to 57%. 

    Schlittler started against the Red Sox four times across the 2026 MLB season: to say he dominated would be an understatement. Over 24 1/3 innings, he posted a 0.74 ERA and struck out 27.

    Yes, Schlittler is the likely Cy Young this season, but Tolle is no slouch — his .199 xBA, 36% chase rate, and 28% K rate this season are among the best in baseball.

    When you tie in their walk rate (both are issuing the free pass at just a 6% clip), each offense will have to earn it. No matter which angle you attack this one at, it smells like an Under. 

    • Time: 8 p.m. ET
    • How to watch: NBC

    More MLB picks for today

    Pick Odds
    CHW ML 47%
    Read analysis in our White Sox vs. Astros predictions

    Odds are correct at the time of publishing and are subject to change.
    Not intended for use in MA.
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    Jon Metler
    Betting Analyst

    Having played, coached, and officiated basketball, Jon naturally turned his focus to the NBA when he entered the sports betting world. With over 15 years of experience, he specializes in spreads, moneylines, and player props—always chasing value through sharp market analysis. A firm believer in analytics, Jon trusts the numbers to guide his bets. He monitors NBA betting markets 365 days a year and uses 10-plus sportsbooks to find the best prices. If there are NBA games on, Jon’s up early, caffeinated, and already placing his favorite bets.

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