Cubs vs. Cardinals Prediction, MLB Picks for Friday, May 29

The first pitch of the Chicago Cubs (31-26) vs. the St. Louis Cardinals (29-25) is set for 7:15 p.m. ET on Friday, May 29, with the Cubs returning a 1.69x payout to win, via PrizePicks.

Both teams have losing records against divisional opponents, but with the NL Central separated by only six games, it’s the most competitive division in the league. 

Below, we'll break down our Cubs vs. Cardinals prediction and picks for Friday’s MLB matchup, including the run line, over/under, and key player picks for PrizePicks.

Make your Cubs vs. Cardinals picks on PrizePicks for tonight's game.

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Cubs vs. Cardinals Prediction, Winner Payout, Over/Under – Friday, May 29

Cubs SP Shota Imanaga (3.52 xFIP across 11 starts and 64.2 IP in 2026) gets the ball on Friday night. Imanaga's last two starts have been a disaster; in 10.1 total innings, he’s allowed 15 earned runs and given up 5 home runs. It’s a mystery why he’s regressed. In his first nine starts of the year, he went a minimum of 6 innings and allowed 2 or fewer earned runs in seven outings. 

Inefficiency is a trend that has impacted the entire Cubs roster. Chicago has plummeted of late, highlighted by an 11-game losing streak and dropping 16 of their last 20 games. 

Thanks to wins in their last two games against the Pirates, the Cubs are alone in second place in the NL Central and just four games behind the Brewers for first place.

The Cardinals will counter with SP Kyle Leahy (4.94 xFIP across 10 starts and 50.2 IP in 2026). Leahy is coming off allowing a season-high 5 earned runs, the third time he’s allowed at least 4 earned runs this season. In the three previous starts, he allowed a combined 3 earned runs.

St. Louis has the opportunity to climb the standings in the NL Central after recently facing the Pirates, Reds, and Brewers, but it couldn’t take advantage, going 2-6 against its division rivals. Despite losing four consecutive games, the Cards remain only 4.5 games out of first place. With a win tonight, they move ahead of the Cubs for second place in the NL Central.

Cubs vs. Cardinals Winner Payout, Over/Under – Friday, May 29

The Cubs enter Friday’s game as road favorites, returning a 1.69x payout if they win outright, via PrizePicks Team Picks.

Here are the full payouts for the Cubs vs. Cardinals game on PrizePicks.

• Spread: Cubs -1.5 (2.22x payout)
• Over/Under: 7.5 (1.75x payout on Over)
• Game Winner Payout: Cubs 1.69x | Cardinals 2.08x

Make your Cubs vs. Cardinals prediction on the winner or over/under on PrizePicks Team Picks to earn real money — available in 35 states!

Team Picks data is live at the time of writing and is subject to change.

Cubs vs. Cardinals Prediction on Spread – 5/29/26

Here are the key game stats and trends behind our Cubs vs. Cardinals prediction on the run line for Friday, May 29.

Lock in your Cubs vs. Cardinals prediction on PrizePicks before the first pitch.

Data used in this article is from Baseball Savant or FanGraphs.

• Imanaga has performed well at Busch Stadium with a 2.31 ERA and 0.51 WHIP in 2 starts.
• Of the 10 Cubs batters Leahy has faced, eight have reached base.
• The Cardinals could find facing the left-handed Imanaga challenging; they have recently struggled against southpaws, ranking 26th in the league in wRC+ (75) since May 1.
• Leahy could struggle to get the Cubs to swing at pitches off the plate, given that his 25.9% chase rate ranks in the 16th percentile. The Cubs sit eighth with a 26.2% chase rate.
• Imanaga ranks in the 98th percentile with a 38.0% chase rate, which could positively impact his performance, with the Cardinals ranking 19th with a 30.7% chase rate.

Cubs vs. Cardinals Player Picks, Stats for PrizePicks – 5/29/26

Here are the top Cubs vs. Cardinals picks to target on PrizePicks for Friday, May 29. Today’s MLB picks for PrizePicks include Michael Busch and Nolan Gorman

Cubs 1B Michael Busch vs. Cardinals: 1.5 Hits + Runs + RBI

• Busch is a career 2 for 5 with a double against Leahy.
• He has been hot recently with 5 hits in his last 18 at-bats, capped by 5 runs scored in the split.
• Busch has improved significantly in May; after posting a .193 BA and .576 OPS in March and April, he has a .286 BA and .986 OPS in May.
• The left-handed-hitting Busch could be trouble for Leahy. Lefties have a .336 BA and .373 BABIP against the Cardinals starter this season.
• Leahy also struggles to find the plate against lefties, with 5.03 walks per nine innings. That could be a challenge against the disciplined Busch, whose 15.6% walk rate ranks in the 96th percentile.

Add Michael Busch to your PrizePicks Lineup now.

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Cardinals 3B Nolan Gorman vs. Cubs: 0.5 Hits

• Gorman is just a career 1 for 8 against Imanaga.
• The Cardinals third baseman is struggling with just 3 hits in his last 30 at-bats.
• Imanaga does well at inducing swing-and-misses with a 31.1% whiff rate that ranks in the 88th percentile. Gorman is at a significant disadvantage, with his 35.9% chase rate ranking in the fourth percentile.
• Imanaga’s second-most thrown pitch is the splitter (35.5%). Gorman has struggled against that pitch; he’s seen it 33 times and has yet to record a hit, with a 46.7% whiff rate.

Add Nolan Gorman to your PrizePicks Lineup now.

Make Cubs vs. Cardinals Picks on PrizePicks

The Cardinals and Cubs will open a three-game series. With Chicago only half a game ahead of St. Louis for second place in the NL Central, we could see a shift in the divisional standings by the end of the weekend.

Don’t wait until the first pitch happens — make your Cubs vs. Cardinals picks on PrizePicks now and earn real money if you’re right.

Pick players, predict More or Less on their stats, and cash in if you’re right. With Team Picks, you can make predictions on game winners, spreads, and over/unders, now available in 35 states.

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