Pirates vs. Cubs Prediction: Can Pittsburgh Solve Paul Skenes’ Wrigley Woes?

The Pirates have nothing to play for and the Cubs still need every win they can find for playoff positioning, but Pittsburgh just spent Friday night reminding everyone it can still bite.

Quick take:

• Pick: Cubs -126 on the moneyline
• Why: Clay Holmes has been Chicago’s steadiest arm all September while Paul Skenes is still hunting consistency
• The number to watch: Skenes has allowed 6 earned runs in 10.2 innings against the Cubs this season

Chicago sits at 82-66, comfortably inside the NL Wild Card picture but still chasing Milwaukee in the Central, currently 9.5 games back with a 2.5-game cushion in the wild card standings. Pittsburgh, at 74-74 and 17.5 games out, is playing out the string with an eye on 2027. That gap in stakes matters, but it hasn’t stopped the Pirates from playing solid baseball lately — they’d won three straight coming into this series before Chicago’s bats woke up in a big way on Friday, pounding out a 12-2 win to snap their own four-game losing skid.

Every game still matters plenty for a Chicago club with its sights set on October, and that’s exactly why a soft spot against a non-contender needs to get fixed fast.

What the Wrigley Field Odds Are Saying

Books have the Cubs as modest home favorites, with moneyline prices hovering around -122 to -126 for Chicago and Pittsburgh sitting in the +104 to +113 range as the road underdog. The run line has the Pirates getting 1.5 runs at a short price, and the total has settled at 8.5, reflecting two lineups that can put runs on the board in a hurry at the Friendly Confines. Given how lopsided Friday’s series opener went, the market isn’t fully buying that the Pirates roll over again — the moneyline gap is notably tighter than a 9.5-game standings gap might suggest. Bettors shopping for the best number on this one can lock in current lines through a DraftKings promo code before first pitch.

Skenes Still Searching for Answers Against Chicago

Paul Skenes takes the ball for Pittsburgh sporting a 10-11 record and a 3.83 ERA with 181 strikeouts across 155 innings, numbers that still undersell how dominant he can be on his best nights. The problem is Chicago has rarely seen his best. Across two starts against the Cubs this season, Skenes has been tagged for six earned runs in 10.2 innings — a rough number relative to his overall body of work, and a trend Pittsburgh needs to snap given how much this lineup has produced against him. He did show signs of turning a corner his last time out, tossing 5.1 scoreless innings against the Angels for his first win since July 19, snapping an 0-3 skid over seven starts in which he’d posted a bloated 5.77 ERA.

Clay Holmes, meanwhile, has quietly been excellent for Chicago, sitting at 6-7 with a 2.83 ERA and a tidy 1.12 WHIP. He’s been the calming presence in a Cubs rotation that has needed one, and against a Pirates offense that’s been streaky all year, that kind of control matters. Chicago’s lineup also has thump up and down it, led by Pete Crow-Armstrong, who’s blossomed into a middle-of-the-order force with 41 home runs and 97 RBIs on the year — the kind of bat that can turn a close game into a laugher in one swing, exactly what happened in Friday’s 12-2 rout.

The two teams have split their season series 5-5, but Chicago has outscored Pittsburgh by a wide margin in the two most recent meetings, winning 11-0 and then edging an 8-7 shootout back in late July.

Pittsburgh isn’t without weapons of its own, even with a banged-up roster. The bullpen has actually been a real strength down the stretch — closer Mason Montgomery has been nearly untouchable, extending a scoreless streak to 20 consecutive appearances with five saves already in September and a perfect 10-for-10 mark in save chances this stretch. That gives the Pirates a real safety net in a tight, low-scoring game, even if this rotation and lineup are dealing with injuries to Braxton Ashcraft, Mitch Keller, Endy Rodríguez, Kirby Yates, and now outfielder Esmerlyn Valdez, who left Friday’s game with a hamstring issue.

That’s a lot of absences for a team trying to steal a series against a club fighting for playoff seeding.

Prediction and Best Bet

Chicago’s lineup depth and Holmes’ recent form give the Cubs the edge in a game where Skenes still has something to prove against this specific opponent. Pittsburgh’s bullpen keeps this from getting out of hand, but the Cubs’ history of getting to Skenes plus their need for wins down the stretch points toward another home win at Wrigley.

The pick:

1. Prediction: Cubs 6, Pirates 3
2. Best Bet: Cubs on the moneyline

With playoff seeding still very much alive for Chicago and a pitching matchup that has favored the Cubs all season, backing the home side at Wrigley is the play.