Chicago Cubs vs. Pittsburgh Pirates Prediction and Picks for Wednesday, September 17th, 2025
Use Code SSWC The MLB action continues on Wednesday with a matinee matchup between the Chicago Cubs (87-64) and the Pittsburgh Pirates (65-87), and we’ve got you covered with our Cubs vs. Pirates prediction. Below, I’ll dive into each team’s recent form and break down the starting pitching matchup, before concluding with picks and predictions on this contest that gets underway at 12:35 ET from PNC Park in Pittsburgh, PA. Read on for free MLB picks on this game, and check out that link for other game breakdowns.
Cubs Comfortably in the Wild Card
The Chicago Cubs have been playing fantastic baseball this season, but there’s just one issue with the organization – they play in the same division as the Brewers. Chicago (87-64) is the third-best team in the N.L., looking up at only Milwaukee (91-59) and Philadelphia (90-61). While a National League Central title may be out of the picture for the Cubs (4.5 GB), they are firmly cemented in the wild card race. Chicago occupies the top spot in the wild card, owning a 9.5-game cushion. In terms of recent form, they’re 6-1 in their last seven games.
The Cubs have won three straight games, including the first two of this series with the Pirates (4-0, 4-1). Cade Horton (5.0 IP, 1 ER) was excellent in his start and earned the win. Brad Keller (1.0 IP, 0 ER) slammed the door in the 9th and picked up his third save of the year. Offensively, Michael Busch homered, while Peter Crow-Armstrong drove in a pair of RBI.
- Matthew Boyd heads to the bump for Wednesday’s series finale, and the 34-year-old hurler has sneakily been one of the better pitchers in the MLB this season.
- Over 29 starts (171.1 IP), the left-hander has gone 13-8 with a 3.05 ERA (13th) and a 1.07 WHIP (13th).
- Boyd last pitched on Friday against the Rays, where he gave up four earned runs on five hits and two walks over 5.0 innings.
- He earned the win in a 6-4 victory.
Pirates in the Cellar of the Central
Meanwhile, it has been another forgettable season for the Pittsburgh Pirates. They have a solid core of young players, but the front office refuses to surround them with quality veteran talent. This has hindered the organization in 2025, as the Buccos are 65-87 and sit 27.0 games out of the divisional race. Only the Nationals (62-89) and Rockies (41-109) are worse in the N.L. Pittsburgh is in the midst of a 1-9 stretch of play, and they’ve lost three straight games.
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It was Paul Skenes (3.2 IP, 3 ER) who got touched up for the loss in Tuesday’s 4-1 defeat against Chicago. Offensively, Pittsburgh only mustered up one run, and it came courtesy of an Oneil Cruz RBI-triple in the 1st inning.
- Johan Oviedo will oppose Boyd on Wednesday, and the 27-year-old starter has looked sharp in six starts (25.2 IP) this year.
- The right-hander is 2-0 with a 2.81 ERA and a 1.17 WHIP.
- Most recently, Oviedo faced the Orioles and held them to two earned runs on five hits and three walks over 5.2 innings.
- It was a no-decision effort in a game that the Buccos lost 3-2.
Cubs vs. Pirates Pick
Moneyline Pick for Cubs vs. Pirates
- Chicago Cubs Moneyline (-150) (5 units)
We’re getting a pretty decent price on the Cubs in this getaway day showdown on Wednesday. I won’t be surprised if this game closes in the -170 range in favor of Chicago.
The Pirates have been in horrendous form recently, going just 1-9 in their last 10 games. They’ll turn to Johan Oviedo, who has been solid with a 2.81 ERA, but is also running into a top-tier Cubs offense. Over the last seven days, Chicago is fourth in wOBA (.349) and 10th in ISO (.173). Additionally, their current roster is slashing .305/.388/.424 against the Oviedo over 59 head-to-head at-bats. I expect the Cubs to provide enough run support for Matthew Boyd (3.05 ERA) and complete the series sweep in Pittsburgh.
Over/Under Pick for Cubs vs. Pirates
- Under 8.0 (-110) (5 units)
While I expect the Cubs to put up a few runs in this game, I still anticipate this game finishing under the total. Oviedo has been so solid this season, posting a 2.81 ERA. In two September starts (10.2 IP), the right-hander owns a 1.69 ERA.
The crux of this bet on the under is Matthew Boyd and his matchup against the lowly Pirates. Pittsburgh has been terrible offensively this season, ranking dead last in runs per game (3.58). Over the last seven days specifically, the Buccos are just 27th in both wOBA (.257) and ISO (.107). During their current 1-9 stretch, Pittsburgh is averaging only 2.4 runs per game. I like for this game to land in the 5-1 or 6-1 range and stay under the number.
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