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Cubs vs Pirates Prediction, Pick, MLB Odds for Wednesday, May 27

Cubs vs Pirates Prediction, Pick, MLB Odds for Wednesday, May 27 article feature image
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Charles LeClaire-Imagn Images. Pictured: Brandon Lowe

The Pittsburgh Pirates host the Chicago Cubs on May 27, 2026. First pitch from PNC Park is scheduled for 6:40 p.m. EDT. The game will be broadcast on SportsNet PT.

The Cubs are favored by -108 on the moneyline and by -1.5 on the run line. The Pirates are -112 on the moneyline and +1.5 on the run line. The total is set at 9 runs.

Find my MLB picks and Cubs vs Pirates prediction below, as well as probable pitchers, weather report, and more.


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Cubs vs Pirates Prediction

  • Cubs vs Pirates Pick: Brandon Lowe Over 1.5 HRR (-135), Cubs Team Total Over (+100)

My Cubs vs Pirates best bet is Brandon Lowe to go over his Hits, Runs, and RBIs total and the Cubs to go over their team total. Make sure to find the best odds by checking our live MLB odds page.


Cubs vs Pirates Odds

Cubs Logo
Wednesday, May 27
6:40 p.m. ET
SportsNet PT
Pirates Logo
Cubs Odds
SpreadTotalMoneyline
-1.5
+142
9
101o / -122u
-108
Pirates Odds
SpreadTotalMoneyline
+1.5
-172
9
101o / -122u
-112
Odds via DraftKings. Get up-to-the-minute MLB odds here.
DraftKings Logo
  • Cubs vs Pirates moneyline: Cubs -108, Pirates -112
  • Cubs vs Pirates over/under: 9 101o / -122u)
  • Cubs vs Pirates spread: Cubs -1.5 (+142), Pirates +1.5 (-172)

Cubs vs Pirates Probable Pitchers

RHP Jameson Taillon (CHC)StatRHP Bubba Chandler (PIT)
2-4W-L1-6
-0.7fWAR (FanGraphs)0.0
5.20/5.23ERA / xERA4.60/4.51
6.46/4.57FIP / xFIP5.25/5.10
12.4%K-BB%6.1%
35.8%GB%34.6%
.235BABIP.228
93Stuff+104
101Location+101

Cubs vs Pirates MLB Betting Preview, Pick

The Pirates are set to host their NL Central foe, the Chicago Cubs, in what will be the third of a four-game homestand at PNC Park in Pittsburgh.

23-year-old right-hander Bubba Chandler will make the start for the Pirates, while the righty veteran James Tallion is scheduled to be on the bump for the visiting Cubs.

In a pitching matchup featuring two starters who have struggled mightily over the course of the 2026 season thus far, I expect Wednesday night’s divisional showdown to deliver several runs for both sides.

Upon making just four starts in 2025 as a rookie, the Pirates’ youngster has allowed a rather troublesome 4.79 ERA on the season thus far. Chandler has allowed a whopping 25 earned runs across 47 frames on the mound in 2026.

Like Chandler, Tallion has also started his 2026 campaign in horrific form, with the Cubs’ 34-year-old right-hander having recorded an even worse ERA than his Wednesday counterpart at 5.20.

That said, I will definitely be targeting some player prop markets on Wednesday night in a matchup featuring two lineups that can get hot at the plate against struggling starting pitchers.

Given that Tallion is pitching in his fourth season in the NL Central, he has a solid history of facing several hitters in the Pirates’ lineup. While I typically favor backing Oneil Cruz at the plate, he is just 1-for-16 against Tallion in his career.

On the other hand, Pirates’ second baseman Brandon Lowe has been far more impressive against the Cubs’ righty, having recorded four hits, two homers and five RBIs across 14 plate appearances against Tallion.

Lowe is also having a phenomenal season at the plate thus far, with the former-Rays slugger having smashed 13 homers on the season, which ranks inside the top-10 in all of baseball.

The Pirates’ lefty has also driven in 32 runners at the plate in 2026 and has absolutely demolished fastball-heavy right-handed pitchers. In fact, the two have actually already met this season in early April, with Lowe having smashed a grand slam versus the Cubs’ veteran.

That said, I will be looking to target Lowe to exceed his 1.5 HRR mark ahead of Wednesday night’s National League contest.

Like Tallion, Chandler has also been very susceptible to heavy damage and hard-contact rates from opposing hitters in 2026. While the Pirates’ young lefty boasts an exceptional four-seam fastball consistently hitting upwards of 100 MPH, he has had significant trouble with his command in 2026.

Despite his fastball's velocity, he consistently struggles to find the strike zone, often falling behind early in the count, resulting in a very high walk rate.

His tendency to fall behind in the count has made his following off-speed pitches far more obvious against major league hitters. While Chandler has a ton of upside with his overpowering high-velocity arsenal, I expect him to get rocked against a stacked Cubs lineup, finding form at the plate.

That said, I will be looking to back the Cubs to exceed their team total as a second betting angle ahead of Wednesday’s matchup.

Picks: Brandon Lowe Over 1.5 HRR (-135), Cubs Team Total Over (+100)


Cubs vs Pirates Weather


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About the Author

Ryan graduated from Providence College in 2016 with Bachelor Degrees in Business Economics & Mathematics. It was at Providence where Ryan really first found his passion for sports betting. For a lifelong sports fan with a knack for statistical analysis, he was instantly drawn to the fundamentals of the industry, specifically how sports betting markets functioned and fluctuated. In what primarily started as a recreational hobby, Ryan began studying the ins-and-outs of sports betting markets on a daily basis. He took to Twitter (now X), where he amassed a following for writing a sports betting blog that provided statistical analysis behind his wagers. In spite of seeking employment opportunities elsewhere post graduation, Ryan continued to follow his passion for the statistical analysis of sports betting wagers, eventually deciding to pursue a career in the sports betting industry.

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