Cubs vs Pirates Prediction, Picks & Odds — Wednesday, September 17

Matthew Boyd has stumbled of late, but the Pirates boast an anemic offense that presents an excellent get-right landing spot for the lefty. The Cubs offense will do its part to take a lead through five innings.

Neil Parker - Analyst at Covers.com
Neil Parker • Betting Analyst
Sep 17, 2025 • 08:20 ET • 4 min read
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This article contains predictions for an old game!

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Matthew Boyd Chicago Cubs MLB
Photo By - Imagn Images. Cubs SP Matthew Boyd (16) throws a pitch at Wrigley Field.

The Chicago Cubs will look to pull off the three-game sweep with an afternoon win over the Pittsburgh Pirates at PNC Park on Wednesday, September 17.

My top Cubs vs. Pirates predictions and MLB picks are calling for the North Siders to pull away from Pittsburgh early and hold on for a convincing victory.

Cubs vs Pirates prediction

Cubs vs Pirates best bet: Cubs first five innings -0.5 (-110)

The Chicago Cubs have been money in the first five innings market while covering the run line in 83 of their last 147 games (+11.80 Units / 7% ROI), and the Pittsburgh Pirates offense ranks last in baseball in wOBA while averaging just 2.93 runs per game in September. 

While Cubs lefty Matthew Boyd has hit a late-season lull with a 5.97 ERA across his past five starts, this is a bounce-back spot, and the Pirates rank 28th in wOBA and 26th in ISO against southpaws for the campaign.

Additionally, Bucs righty Johan Oviedo has benefited from good luck on the hill while holding opposing hitters to a minuscule .230 BABIP. His 4.55 xFIP is also miles above his 2.81 ERA, and this will be his 10th start and 11th career appearance against the Cubbies, so the Chicago lineup has familiarity against him.

Chicago also ranks eighth in wOBA and sixth in ISO against righties for the campaign and is beginning to show signs of life at the dish again with a ninth-ranked overall wOBA in September.

Cubs vs Pirates same-game parlay (SGP)

The Pirates don't pack enough punch to keep pace with the Cubs, and Chicago will put runs on the board against Oviedo.

Still, I don't expect a high-scoring tilt because both clubs have trended to the Under.

Chicago has gone Under the number in 52 of its last 92 games (+13.55 Units / 13% ROI), while the Under has hit in 82 of Pittsburgh's 140 games (+25.10 Units / 16% ROI).

Cubs vs Pirates SGP

  • Cubs F5 -0.5 
  • Cubs -1.5
  • Under 8.0

Cubs vs Pirates odds

  • Moneyline: Chicago -150 | Pittsburgh +125
  • Run line: Chicago -1.5 (+110) | Pittsburgh +1.5 (-135)
  • Over/Under: Over 8 (-105) | Under 8 (-115)

Cubs vs Pirates trend

The Chicago Cubs have covered the 1st five innings run line in 83 of their last 147 games (+11.80 Units / 7% ROI). Find more MLB betting trends for Cubs vs. Pirates.

How to watch Cubs vs Pirates and game info

Location PNC Park, Pittsburgh, PA
Date Wednesday, September 17, 2025
First pitch 12:35 p.m. ET
TV MARQ, SNP, MLBN
Cubs starting pitcher Matthew Boyd
(13-8, 3.05 ERA)
Pirates starting pitcher Johan Oviedo
(2-0, 2.81 ERA)

Cubs vs Pirates latest injuries

Cubs vs Pirates weather

Odds are correct at the time of publishing and are subject to change.
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Neil Parker - Covers
Betting Analyst

Neil Parker is, first and foremost, a sports fan. A huge supporter of the Cowboys, Cubs, and Maple Leafs, he has managed to parlay his passion into writing gigs at some of the top websites in the industry.

Neil takes a numbers-based approach to his handicapping and complements his in-depth statistical analysis with a keen eye on the markets to provide the best available odds. He loves to lean on his rolodex of idioms to offset his inner nerd. When it comes to wagering, he throws down on anything that catches his eye at bet365, Betway and BetVictor. He also keeps a close eye on CoolBet because the polar bear brand often has outlier NHL and NFL moneyline prices.

Neil graduated with honors from St. Thomas University in 2007 before completing his BEd at Acadia University in 2010. After teaching a myriad of courses and subjects, he found a groove delivering fun lessons to exceptional learners in non-traditional classroom environments. If his decade-plus teaching run taught him anything about sports betting, it’s to stay the course and use the summer – or offseason – to refresh and prepare to be better in the year to come.

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